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In the title complex salt, (C6H6N5)2[ZnCl4], the ZnII cation is coordinated by four chloride ligands in a distorted tetra­hedral geometry. The organic cations and complex anions are connected by N-H...Cl hydrogen bonds, leading to the formation of a three-dimensional network. The title complex salt was synthesized by the reaction of sodium azide, pyridine-2-carbo­nitrile and ZnCl2 in aqueous solution. The salt was characterized by elemental analysis and IR and UV-Vis spectroscopy.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113010809/sf3195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113010809/sf3195Isup2.hkl
Contains datablock I

CCDC reference: 893243

Comment top

During the last decade, the number of reports describing the synthesis and properties of tetrazoles and their complexes has increased dramatically. Tetrazoles are very attractive due to their wide application, for example, in medicinal chemistry (Dhayanithi et al., 2011), coordination chemistry (Bhandari et al., 1998, 2000; Janiak, 1994; Janiak et al., 1995, 1996; Zhou et al., 1998), materials chemistry (Hill et al., 1996; Zhang et al., 2010) and, last but not least, as highly energetic compounds possessing military applications (Carlucci et al., 1999; Ostrovskii et al., 1999; Piekiel & Zachariah, 2012). Tetrazoles may coordinate transition metal ions, forming complexes which can be used as phase transition dielectric materials for applications in micro-electronics and memory storage (Fu et al., 2007, 2008; Fu & Xiong, 2008; Zhao et al., 2008).

The general method of synthesis reported previously is based on the reaction of azides with organic nitriles in the presence of metal catalysts (Demko & Sharpless, 2001a,b, 2002a,b). This method requires solvothermal conditions or at least heating in solvents of high boiling point, such as dimethylformamide (Demko & Sharpless, 2001a,b). This type of procedure is not safe because of the metal azides or HN3 which can be formed. Because of this problem, zinc was used at the very beginning of tetrazole synthesis, as zinc azides are not very sensitive towards detonation; moreover, the earliest reactions were performed in neutral or slightly alkaline media to avoid HN3 evolution. Recently, new methods of tetrazole synthesis, including LiCl instead of Zn or W (He et al., 2009), have been proposed. Nevertheless, a high temperature is still necessary to perform these reactions.

In this paper, we report a simple and safe method for the preparation of a tetrazole complex by the reaction of sodium azide, nitrile and zinc chloride in water at room temperature (see scheme). We characterized the title compound, (I), by elemental analysis and IR and UV–Vis spectroscopy. A crystal of (I) suitable for X-ray analysis was selected from the materials prepared as decribed in the Experimental section. Single-crystal X-ray analysis reveals that (I) crystallizes in the triclinic space group P1. The asymmetric unit is composed of two organic cations and one [ZnCl4]2- anion (Fig. 1), and the crystal packing along b is presented in Fig. 2. In each cation, the pyridine N atom (N11 and N22) is protonated. In the anion, atom Zn1 is coordinated by four chloride ligands in a distorted tetrahedral geometry. Selected bond distances and angles are listed in Table 1. The Cl—Zn—Cl angles are in the range 105.13 (4)–116.09 (3)°. All Zn—Cl bond lengths are different as a result of hydrogen-bond formation (Fig. 3 and Table 2). Atom Cl1 forms a medium-strength hydrogen bond to atom N11 and a weak hydrogen bond to atom N22, while atoms Cl2 and Cl4 each form only weak hydrogen bonds to atoms N2 and N13, respectively (Desiraju & Steiner, 1999; Jeffrey, 1997). Atom Cl3 is not involved in hydrogen bonding, so the Zn—Cl3 distance is the shortest, while Zn—Cl1 is the longest. These interactions create a three-dimensional network (Fig. 4). It can be seen that the hydrogen-bonding network forms layers between which there are no specific interactions.

The IR spectrum of (I) is shown in Fig. 5. The absence of bands in the characteristic range for νCN in pyridine-2-carbonitrile, and the formation of new bands at 1636 and 1282 cm-1 [which can be attributed to the ν(C N) and ν(N—NN–) vibrations in the tetrazole ring, respectively], confirm the formation of tetrazole in (I) (Wang et al., 2011). Bands at 3250 and 3081 cm-1 and at 3053 and 2988 cm-1 confirm the presence of N—H vibrations for the pyridine and tetrazole rings, respectively. In the UV part of the reflectance spectrum of (I) (Fig. 6), two bands are observed at 277 and 237 nm, which may be assigned to an intraligand (IL) ππ* transition (Tong & Xin, 2011).

Related literature top

For related literature, see: Bhandari et al. (1998, 2000); Carlucci et al. (1999); Demko & Sharpless (2001a, 2001b, 2002a, 2002b); Desiraju & Steiner (1999); Dhayanithi et al. (2011); Fu & Xiong (2008); Fu et al. (2007); Fu, Zhang & Xiong (2008); He et al. (2009); Hill et al. (1996); Janiak (1994); Janiak et al. (1995, 1996); Jeffrey (1997); Ostrovskii et al. (1999); Piekiel & Zachariah (2012); Tong & Xin (2011); Wang et al. (2011); Zhang et al. (2010); Zhao et al. (2008); Zhou et al. (1998).

Experimental top

All chemicals were of analytical grade (Aldrich) and were used without further purification. CHN microanalyses were performed using a Vario Micro Cube elemental analyser. The IR spectrum was recorded on a Nicolet iS5 55 FT–IR spectrophotometer. Diffuse reflectance spectra were measured in BaSO4 pellets with BaSO4 as a reference using a Shimadzu UV-3600 equipped with an ISR-3100 attachment.

ZnCl2 (0.645 g, 5.0 mmol), NaN3 (0.65 g, 10.0 mmol) and pyridine-2-carbonitrile (1.04 g, 10.0 mmol) were dissolved in water (150 ml) and the mixture was stirred for 4 d at room temperature. After that time, a white compound was filtered off, washed with water and dried in air (yield: 0.76 g, 35%). 2 M HCl was then added dropwise to the compound (0.25 g) until the solid dissolved, and the solution was extracted with CH2Cl2 (ca 5 ml). The organic phase was separated from the inorganic phase and the inorganic phase was left aside for crystallization. The product, (I), was filtered off and dried in air (yield 0.10 g, 30%). Analysis, calculated for C12H12Cl4N10Zn: C 28.62, H 2.40, N 27.82%; found: C 28.33, H 2.39, N 27.14%. Spectroscopic analysis: IR (Medium?, ν, cm-1): 3250, 3081, 3053, 2988, 1705, 1636, 1611, 1458, 1282, 1035, 805, 792, 748, 713, 621; UV–Vis (BaSO4 pellet, λ, nm): 277, 237.

Refinement top

All C-bound H atoms were positioned with an idealized geometry, with C—H = 0.93 Å [Added text OK?] and refined using a riding model, with Uiso(H) = 1.5Ueq(C) for methyl groups and 1.2Ueq(C) otherwise. N-bound H atoms were found in difference Fourier maps and refined without any restraints.

Computing details top

Data collection: CrysAlis RED (Oxford Diffraction, 2011); cell refinement: CrysAlis RED (Oxford Diffraction, 2011); data reduction: CrysAlis PRO (Oxford Diffraction, 2011); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The components of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Atom labels should not touch atoms or bonds - please revise]
[Figure 2] Fig. 2. A view of the packing of (I), along the b axis.
[Figure 3] Fig. 3. A view of the hydrogen-bonding (thin lines) in (I).
[Figure 4] Fig. 4. A view of the arrangement of anions and cations in (I). Dotted lines represent hydrogen bonds. [OK?]
[Figure 5] Fig. 5. The IR spectrum of (I) in the 4000–550 cm-1 region.
[Figure 6] Fig. 6. The reflectance spectrum of (I) in BaSO4 after Kubelka–Munk transformation.
Bis[2-(2H-tetrazol-5-yl)pyridinium] tetrachloridozincate(II) top
Crystal data top
(C6H6N5)2[ZnCl4]Z = 2
Mr = 503.49F(000) = 504
Triclinic, P1Dx = 1.687 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 9.196 (5) ÅCell parameters from 0 reflections
b = 10.491 (5) Åθ = 0–0°
c = 11.186 (5) ŵ = 1.80 mm1
α = 102.407 (5)°T = 293 K
β = 98.185 (5)°Prism, colourless
γ = 105.697 (5)°0.55 × 0.49 × 0.21 mm
V = 991.3 (8) Å3
Data collection top
Oxford SuperNova
diffractometer
4101 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3266 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 10.3756 pixels mm-1θmax = 26.5°, θmin = 3.2°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2011)
k = 1313
Tmin = 0.438, Tmax = 0.704l = 1414
12476 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0302P)2]
where P = (Fo2 + 2Fc2)/3
4101 reflections(Δ/σ)max = 0.001
260 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
(C6H6N5)2[ZnCl4]γ = 105.697 (5)°
Mr = 503.49V = 991.3 (8) Å3
Triclinic, P1Z = 2
a = 9.196 (5) ÅMo Kα radiation
b = 10.491 (5) ŵ = 1.80 mm1
c = 11.186 (5) ÅT = 293 K
α = 102.407 (5)°0.55 × 0.49 × 0.21 mm
β = 98.185 (5)°
Data collection top
Oxford SuperNova
diffractometer
4101 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2011)
3266 reflections with I > 2σ(I)
Tmin = 0.438, Tmax = 0.704Rint = 0.032
12476 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.30 e Å3
4101 reflectionsΔρmin = 0.27 e Å3
260 parameters
Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Positions of all of non-hydrogen atoms were determined by direct methods using SIR97 (Altomare et al., 1999). All non-hydrogen atoms were refined anisotropically using weighted full-matrix least-squares on F2. Refinement and further calculations were carried out using SHELXL97 (Sheldrick, 2008).

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 > 2σ(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
Zn10.26396 (3)0.75957 (2)0.25111 (2)0.04205 (10)
Cl10.47346 (6)0.76958 (5)0.40002 (5)0.04462 (14)
Cl20.13410 (6)0.89224 (5)0.34664 (6)0.04824 (15)
Cl30.35100 (8)0.82995 (7)0.09271 (6)0.06294 (18)
Cl40.10036 (7)0.53960 (6)0.20200 (6)0.05392 (17)
N10.1412 (2)0.2519 (2)0.4684 (2)0.0555 (5)
N20.0982 (3)0.3215 (2)0.5622 (2)0.0604 (6)
N30.1638 (3)0.4555 (2)0.5919 (2)0.0712 (6)
N40.2549 (3)0.4764 (2)0.5123 (2)0.0639 (6)
C50.2385 (3)0.3523 (2)0.4392 (2)0.0452 (5)
C60.3207 (2)0.3323 (2)0.3387 (2)0.0426 (5)
C70.3255 (3)0.2076 (2)0.2712 (2)0.0559 (6)
H70.27250.12650.28780.067*
C80.4101 (3)0.2046 (3)0.1783 (3)0.0610 (7)
H80.41270.12080.13160.073*
C90.4906 (3)0.3246 (3)0.1543 (2)0.0579 (7)
H90.5490.32290.09290.069*
C100.4823 (3)0.4460 (3)0.2231 (2)0.0528 (6)
H100.53450.52830.20810.063*
N110.3997 (2)0.4464 (2)0.31149 (19)0.0447 (5)
H20.031 (3)0.275 (3)0.603 (3)0.098 (11)*
H110.400 (3)0.520 (2)0.355 (2)0.059 (8)*
N120.1239 (2)0.2044 (2)0.95795 (18)0.0517 (5)
N130.1579 (3)0.3387 (2)0.9786 (2)0.0582 (6)
N140.2489 (3)0.3944 (2)0.9113 (2)0.0641 (6)
N150.2768 (2)0.2908 (2)0.83919 (19)0.0546 (5)
C160.2007 (2)0.1774 (2)0.8692 (2)0.0428 (5)
C170.2047 (2)0.0418 (2)0.8078 (2)0.0414 (5)
C180.1395 (3)0.0782 (3)0.8379 (2)0.0561 (6)
H180.08470.07840.90160.067*
C190.1568 (3)0.1988 (3)0.7717 (3)0.0672 (7)
H190.11410.28030.79210.081*
C200.2353 (3)0.2001 (3)0.6771 (3)0.0610 (7)
H200.24480.28190.6320.073*
C210.2999 (3)0.0793 (2)0.6495 (2)0.0537 (6)
H210.3550.07760.5860.064*
N220.2829 (2)0.0360 (2)0.71483 (18)0.0447 (5)
H130.127 (2)0.386 (2)1.032 (2)0.043 (7)*
H220.326 (3)0.107 (2)0.700 (2)0.058 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04800 (17)0.03893 (16)0.04320 (16)0.01448 (12)0.01712 (12)0.01306 (12)
Cl10.0479 (3)0.0422 (3)0.0453 (3)0.0127 (2)0.0125 (3)0.0147 (2)
Cl20.0553 (3)0.0382 (3)0.0594 (4)0.0185 (3)0.0259 (3)0.0159 (3)
Cl30.0851 (5)0.0702 (4)0.0479 (4)0.0301 (4)0.0316 (3)0.0263 (3)
Cl40.0527 (4)0.0381 (3)0.0653 (4)0.0091 (3)0.0185 (3)0.0047 (3)
N10.0540 (12)0.0517 (12)0.0677 (14)0.0125 (10)0.0245 (11)0.0273 (11)
N20.0571 (14)0.0657 (16)0.0637 (15)0.0095 (12)0.0224 (12)0.0342 (12)
N30.0846 (17)0.0639 (16)0.0650 (15)0.0115 (13)0.0357 (13)0.0187 (12)
N40.0827 (16)0.0516 (13)0.0587 (13)0.0088 (11)0.0378 (12)0.0182 (11)
C50.0457 (13)0.0444 (13)0.0489 (14)0.0111 (11)0.0110 (11)0.0225 (11)
C60.0432 (13)0.0393 (12)0.0497 (13)0.0133 (10)0.0106 (11)0.0200 (10)
C70.0649 (16)0.0394 (13)0.0654 (17)0.0147 (12)0.0127 (14)0.0206 (12)
C80.0731 (18)0.0528 (16)0.0618 (17)0.0324 (14)0.0123 (14)0.0102 (13)
C90.0605 (16)0.0672 (17)0.0577 (16)0.0308 (14)0.0230 (13)0.0199 (13)
C100.0566 (15)0.0532 (15)0.0584 (15)0.0188 (12)0.0258 (13)0.0239 (12)
N110.0520 (12)0.0384 (11)0.0513 (12)0.0172 (10)0.0208 (10)0.0172 (10)
N120.0534 (12)0.0590 (13)0.0493 (12)0.0218 (10)0.0193 (10)0.0173 (10)
N130.0661 (15)0.0639 (15)0.0563 (14)0.0326 (12)0.0286 (12)0.0140 (12)
N140.0735 (15)0.0576 (14)0.0729 (15)0.0276 (12)0.0330 (13)0.0210 (12)
N150.0632 (13)0.0484 (12)0.0623 (13)0.0228 (10)0.0300 (11)0.0175 (10)
C160.0411 (12)0.0520 (14)0.0390 (12)0.0153 (11)0.0133 (10)0.0159 (11)
C170.0382 (12)0.0491 (13)0.0366 (12)0.0101 (10)0.0079 (10)0.0151 (10)
C180.0572 (16)0.0578 (16)0.0573 (16)0.0109 (13)0.0206 (13)0.0270 (13)
C190.0677 (18)0.0463 (15)0.080 (2)0.0030 (13)0.0075 (16)0.0253 (14)
C200.0666 (18)0.0425 (14)0.0659 (18)0.0150 (13)0.0056 (14)0.0059 (13)
C210.0572 (15)0.0526 (15)0.0470 (14)0.0175 (12)0.0106 (12)0.0043 (12)
N220.0497 (12)0.0392 (11)0.0447 (11)0.0092 (10)0.0151 (9)0.0128 (9)
Geometric parameters (Å, º) top
Zn1—Cl12.3236 (11)C10—H100.93
Zn1—Cl22.2648 (9)N11—H110.82 (2)
Zn1—Cl32.2297 (10)N12—N131.318 (3)
Zn1—Cl42.2873 (11)N12—C161.323 (3)
N1—C51.318 (3)N13—N141.308 (3)
N1—N21.317 (3)N13—H130.83 (2)
N2—N31.317 (3)N14—N151.317 (2)
N2—H20.92 (3)N15—C161.343 (3)
N3—N41.318 (3)C16—C171.453 (3)
N4—C51.337 (3)C17—N221.347 (3)
C5—C61.451 (3)C17—C181.374 (3)
C6—N111.342 (3)C18—C191.383 (3)
C6—C71.379 (3)C18—H180.93
C7—C81.384 (3)C19—C201.364 (4)
C7—H70.93C19—H190.93
C8—C91.379 (3)C20—C211.366 (4)
C8—H80.93C20—H200.93
C9—C101.367 (3)C21—N221.333 (3)
C9—H90.93C21—H210.93
C10—N111.331 (3)N22—H220.81 (2)
Cl3—Zn1—Cl2112.68 (3)C10—N11—C6123.8 (2)
Cl3—Zn1—Cl4116.09 (3)C10—N11—H11118.8 (18)
Cl2—Zn1—Cl4105.13 (4)C6—N11—H11117.3 (18)
Cl3—Zn1—Cl1108.78 (4)N13—N12—C16100.4 (2)
Cl2—Zn1—Cl1107.68 (4)N14—N13—N12115.7 (2)
Cl4—Zn1—Cl1106.00 (3)N14—N13—H13121.4 (16)
C5—N1—N2100.9 (2)N12—N13—H13122.8 (16)
N3—N2—N1114.8 (2)N13—N14—N15104.8 (2)
N3—N2—H2125.5 (18)N14—N15—C16106.38 (19)
N1—N2—H2119.6 (18)N12—C16—N15112.6 (2)
N2—N3—N4105.2 (2)N12—C16—C17125.4 (2)
N3—N4—C5106.1 (2)N15—C16—C17122.0 (2)
N1—C5—N4113.1 (2)N22—C17—C18118.0 (2)
N1—C5—C6124.2 (2)N22—C17—C16115.8 (2)
N4—C5—C6122.7 (2)C18—C17—C16126.1 (2)
N11—C6—C7118.1 (2)C17—C18—C19118.9 (2)
N11—C6—C5116.25 (19)C17—C18—H18120.6
C7—C6—C5125.6 (2)C19—C18—H18120.6
C6—C7—C8119.1 (2)C20—C19—C18121.1 (3)
C6—C7—H7120.4C20—C19—H19119.5
C8—C7—H7120.4C18—C19—H19119.5
C9—C8—C7120.8 (2)C19—C20—C21119.0 (2)
C9—C8—H8119.6C19—C20—H20120.5
C7—C8—H8119.6C21—C20—H20120.5
C10—C9—C8118.2 (2)N22—C21—C20119.1 (2)
C10—C9—H9120.9N22—C21—H21120.4
C8—C9—H9120.9C20—C21—H21120.4
N11—C10—C9120.0 (2)C21—N22—C17124.0 (2)
N11—C10—H10120C21—N22—H22117.8 (17)
C9—C10—H10120C17—N22—H22118.1 (17)
C5—N1—N2—N30.7 (3)C16—N12—N13—N140.6 (3)
N1—N2—N3—N40.6 (3)N12—N13—N14—N150.8 (3)
N2—N3—N4—C50.2 (3)N13—N14—N15—C160.6 (3)
N2—N1—C5—N40.6 (3)N13—N12—C16—N150.2 (3)
N2—N1—C5—C6179.6 (2)N13—N12—C16—C17179.4 (2)
N3—N4—C5—N10.2 (3)N14—N15—C16—N120.3 (3)
N3—N4—C5—C6179.9 (2)N14—N15—C16—C17179.9 (2)
N1—C5—C6—N11171.7 (2)N12—C16—C17—N22176.4 (2)
N4—C5—C6—N118.4 (3)N15—C16—C17—N223.2 (3)
N1—C5—C6—C79.1 (4)N12—C16—C17—C185.1 (4)
N4—C5—C6—C7170.8 (2)N15—C16—C17—C18175.3 (2)
N11—C6—C7—C80.3 (3)N22—C17—C18—C190.1 (3)
C5—C6—C7—C8179.5 (2)C16—C17—C18—C19178.6 (2)
C6—C7—C8—C90.9 (4)C17—C18—C19—C200.8 (4)
C7—C8—C9—C101.1 (4)C18—C19—C20—C211.2 (4)
C8—C9—C10—N110.8 (4)C19—C20—C21—N220.7 (4)
C9—C10—N11—C60.2 (4)C20—C21—N22—C170.1 (4)
C7—C6—N11—C100.0 (3)C18—C17—N22—C210.5 (3)
C5—C6—N11—C10179.2 (2)C16—C17—N22—C21179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl2i0.92 (3)2.22 (3)3.105 (3)162 (3)
N11—H11···Cl10.82 (2)2.44 (2)3.171 (3)150 (2)
N13—H13···Cl4ii0.83 (2)2.30 (2)3.112 (2)167 (2)
N22—H22···Cl1iii0.81 (2)2.50 (3)3.210 (2)147 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula(C6H6N5)2[ZnCl4]
Mr503.49
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.196 (5), 10.491 (5), 11.186 (5)
α, β, γ (°)102.407 (5), 98.185 (5), 105.697 (5)
V3)991.3 (8)
Z2
Radiation typeMo Kα
µ (mm1)1.80
Crystal size (mm)0.55 × 0.49 × 0.21
Data collection
DiffractometerOxford SuperNova
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2011)
Tmin, Tmax0.438, 0.704
No. of measured, independent and
observed [I > 2σ(I)] reflections
12476, 4101, 3266
Rint0.032
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.070, 1.03
No. of reflections4101
No. of parameters260
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: CrysAlis RED (Oxford Diffraction, 2011), CrysAlis PRO (Oxford Diffraction, 2011), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), WinGX (Farrugia, 2012).

Selected geometric parameters (Å, º) top
Zn1—Cl12.3236 (11)C6—N111.342 (3)
Zn1—Cl22.2648 (9)N11—H110.82 (2)
Zn1—Cl32.2297 (10)N12—N131.318 (3)
Zn1—Cl42.2873 (11)N12—C161.323 (3)
N1—C51.318 (3)N13—N141.308 (3)
N1—N21.317 (3)N13—H130.83 (2)
N2—N31.317 (3)N14—N151.317 (2)
N2—H20.92 (3)N15—C161.343 (3)
N3—N41.318 (3)N22—H220.81 (2)
N4—C51.337 (3)
Cl3—Zn1—Cl2112.68 (3)N3—N4—C5106.1 (2)
Cl3—Zn1—Cl4116.09 (3)N11—C6—C5116.25 (19)
Cl2—Zn1—Cl4105.13 (4)C6—N11—H11117.3 (18)
Cl3—Zn1—Cl1108.78 (4)N13—N12—C16100.4 (2)
Cl2—Zn1—Cl1107.68 (4)N14—N13—N12115.7 (2)
Cl4—Zn1—Cl1106.00 (3)N13—N14—N15104.8 (2)
C5—N1—N2100.9 (2)N14—N15—C16106.38 (19)
N3—N2—N1114.8 (2)N22—C17—C16115.8 (2)
N2—N3—N4105.2 (2)C17—N22—H22118.1 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl2i0.92 (3)2.22 (3)3.105 (3)162 (3)
N11—H11···Cl10.82 (2)2.44 (2)3.171 (3)150 (2)
N13—H13···Cl4ii0.83 (2)2.30 (2)3.112 (2)167 (2)
N22—H22···Cl1iii0.81 (2)2.50 (3)3.210 (2)147 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+1.
 

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