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The title salt, (C5H5N4S)2[ZnCl4], consists of two 6-thioxo-1,6-dihydro­purinium (6mpH2+) cations (A and B) and a tetra­chloro­zincate anion, which are held together by N-H...Cl and C-H...Cl inter­actions. There is an anion-[pi] inter­action between one Cl atom of the [ZnCl4]- anion and the pyrimidine ring of the 6mpH2+(B) cation. Inter­molecular [pi]-[pi] stacking inter­actions allow 6mpH2+(A) cations to form anti­parallel pairs. One inter­esting structural feature is the double N-H...N inter­molecular hydrogen bonds between two 6mpH2+(A) cations. This kind of inter­action, mimicking that of natural nucleobases, can be very valuable in designing new therapeutic purine derivatives.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106019469/ob3005sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106019469/ob3005Isup2.hkl
Contains datablock I

CCDC reference: 616111

Comment top

6-Mercaptopurine (6 m pH; 1,7-dihydro-6H-purine-6-thione) exists in solid and liquid states in the 6-thione form. It has also a tautomeric imine proton equilibrium between positions 7 and 9 of the imidazole ring (Pazderski et al., 2006), being found in the N9—H form in anhydrous 6 m pH (Gyr, 1991) but in the N7—H form in 6-mercaptopurine monohydrate (see the first scheme below) (Sletten et al., 1969; Brown, 1969). The 6-thioxo-1,6-dihydropurinium cation (6 m pH2+), in which both the N7 and the N9 positions are protonated and the positive charge is shared by the imidazole N atoms, was previously confirmed by single-crystal X-ray diffraction and vibrational spectroscopy of 6-thioxo-1,6-dihydropurinium chloride (Perez-Ruiz et al., 1998).

Preparation and structural characterization of complexes of biologically active metals, such as zinc, with purines is one of our recent interests. In an attempt to prepare the zinc analogue of bis(6-mercaptopurinato)mercury(II) (Lavertue et al., 1976), we obtained to the title salt, (I).

There are two crystallographically independent, planar 6 m pH2+ cations and one tetrachlorozincate anion in the asymmetric unit (Fig. 1). The pyrimidine H atoms of the 6 m pH2+ cations A and B are involved in N1—H···Cl3 and N21—H···Cl2 hydrogen bonds, the latter being much weaker (Desiraju & Steiner, 1999), as seen from Table 2. There is also a weak, short C—H···Cl contact between C2 and Cl2, generating an R22(7) graph-set motif (Bernstein et al., 1995) with an N1—H···Cl2 hydrogen bond.

The 6 m pH2+ cations can form pairs in the crystalline state, regardless of the electrostatic force between their positive charges. Repulsion of similar charges is reduced by antiparallel geometry, and the cations are held together by ππ stacking and possibly also by cation–π interactions (Meyer et al., 2003). Such a pair of antiparallel displaced 6 m pH2+(A) cations can be observed in Fig. 2 around (1/2, 1/2, 1) with an interplanar distance of 3.447 (3) Å. The centroid-to-centroid distance of the six-membered aromatic rings is 3.584 (3) Å. Cation–π interactions in this pair may also exist, but because of the partial overlap of the 6 m pH2+(A) cations with positive charges at two ends, such interactions are not favoured. There is no 6 m pH2+(B) pair that has a rational centroid-to-centroid distance, but the 6 m pH2+(B) cation participates in anion–π interaction with atom Cl1 (Fig. 1). The distance between the centroid of the pyrimidine ring and atom Cl1 is 3.247 (3) Å, being slightly longer than that observed in the 1,3,5-triazine complex (Demeshko, et al., 2004). The angle between the Cl1···centroid axis and the plane of the pyrimidine ring is 85°, and the Cl1···centroid axis points away from atoms N21 and N23.

Previous studies of tetrachlorozincates have shown that the Zn—Cl bond lengths are not identical (Parvez & Sabir, 1998; García-Raso et al., 1999). The environment around the anion, as well as hydrogen bonds or repulsions, influences appreciably the Zn—Cl bond lengths and Cl—Zn—Cl bond angles. In (I), however, no clear trend of such influences was detected (Table 1). For example, the fact that the Zn—Cl4 bond is the longest does not meet the expectations derived from hydrogen bonding effects (Table 2), because atom Cl4 accepts only one, rather weak, N—H···Cl contact.

Imidazole atoms N7 and N9 in the 6 m pH2+ cation share the positive charge (Perez-Ruiz et al., 1998). Therefore, the bonds involving atoms N7 and N9, as well as N27 and N29, in (I) are expected to be of about equal length. In fact, the N7—C8 and N27—C28 bonds (Table 1) are comparable to the N7—C8 distance in 6 m pH2Cl (Pazderski et al., 2006), and the N9—C8 and N29—C28 bonds are slightly longer than the N7—C8 and N27—C28 bonds. However, all of these bond lengths in (I) are closer to one another than the analogous bonds in 6 m pH·H2O and in anhydrous 6 m pH (Pazderski et al., 2006; Gyr, 1991). One interesting structural feature involving the imidazole N atoms is the double N9—H9···N3 intermolecular hydrogen-bond system between two 6 m pH2+(A) cations (shown at the centre of Fig. 2), generating an R22(8) graph-set motif. These cations are in the same plane and related by an inversion centre.

Sulfur is a weak atomic acceptor and it is often superseded in hydrogen-bond formation because of the presence of stronger acceptors (Desiraju & Steiner, 1999). Certainly, some such interactions, e.g. N—H···S (Dubler & Gyr, 1988) and C—H···S (Cini et al., 2000), have been reported for 6 m pH compounds, but they are rather unusual. In (I), there is possibly a very weak C28—H28···S26v interaction (Table 2). Atom S26 also forms a short contact, 3.3929 (12) Å, to Cl4 at (−x, 1/2 + y, 3/2 − z), which is shorter than the sum of van der Waals radii (3.55 Å).

Experimental top

6-Mercaptopurine monohydrate (119 mg, 0.70 mmol) and zinc chloride (48 mg, 0.35 mmol) were dissolved in water (50 ml). The mixture was stirred at room temperature for one hour, then aqueous 2M HCl (20 ml) was added and the resulting solution was left to stand. After one week, some crystals and a yellow [or white?] powder were formed, and these were removed from the solution; the powder was found to be mostly 6-thioxo-1,6-dihydropurinium chloride, and the crystals were found to be 6-mercaptopurine monohydrate. After slow evaporation of the solution at room temperature over a period of three months, only a few colourless crystals of (I) were obtained. A similar synthetic route was also tested with cobalt(II) and cadmium(II) chlorides without any success.

Refinement top

All H atoms were found in difference density maps, but were placed in ideal calculated positions and allowed to ride on their parent atoms at distances of 0.88 (N—H) and 0.95 Å (C—H), with Uiso(H) of 1.2Ueq(C,N).

Computing details top

Data collection: Collect (Bruker, 2004); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SIR2002 (Burla, et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The 6 m pH2+ and [ZnCl4]2− components of (I), showing the atom-labelling scheme. Displacement ellipsoids were drawn at the 50% probability level and non-covalent interactions are illustrated with dashed lines.
[Figure 2] Fig. 2. The packing of (I), viewed along the b axis. Hydrogen bonds are illustrated with dashed lines. Symmetry code: (i) −x + 1, y − 1/2, −z + 3/2.
Bis(6-thioxo-1,6-dihydropurinium) tetrachlorozincate(II) top
Crystal data top
(C5H5N4S)2[ZnCl4]F(000) = 1024
Mr = 513.55Dx = 1.851 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 16093 reflections
a = 17.1397 (5) Åθ = 0.4–28.3°
b = 6.8500 (2) ŵ = 2.15 mm1
c = 16.1142 (5) ÅT = 173 K
β = 103.021 (2)°Block, colourless
V = 1843.27 (10) Å30.25 × 0.15 × 0.15 mm
Z = 4
Data collection top
Bruker Kappa APEX-II
diffractometer
4528 independent reflections
Radiation source: fine-focus sealed tube3408 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
Detector resolution: 9 pixels mm-1θmax = 28.3°, θmin = 2.4°
ϕ and ω scansh = 2222
Absorption correction: multi-scan
(MULABS in PLATON; Blessing, 1995; Spek, 2003)
k = 98
Tmin = 0.603, Tmax = 0.724l = 1921
27322 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0145P)2 + 3.7658P]
where P = (Fo2 + 2Fc2)/3
4528 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
(C5H5N4S)2[ZnCl4]V = 1843.27 (10) Å3
Mr = 513.55Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.1397 (5) ŵ = 2.15 mm1
b = 6.8500 (2) ÅT = 173 K
c = 16.1142 (5) Å0.25 × 0.15 × 0.15 mm
β = 103.021 (2)°
Data collection top
Bruker Kappa APEX-II
diffractometer
4528 independent reflections
Absorption correction: multi-scan
(MULABS in PLATON; Blessing, 1995; Spek, 2003)
3408 reflections with I > 2σ(I)
Tmin = 0.603, Tmax = 0.724Rint = 0.087
27322 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.05Δρmax = 0.44 e Å3
4528 reflectionsΔρmin = 0.44 e Å3
226 parameters
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
Zn10.23591 (2)0.37451 (6)0.71080 (3)0.02477 (11)
Cl10.17815 (5)0.39452 (13)0.57077 (5)0.02776 (19)
Cl20.24644 (5)0.66457 (13)0.78154 (5)0.02746 (19)
Cl30.35860 (5)0.23304 (13)0.72793 (6)0.0311 (2)
Cl40.15987 (5)0.17928 (13)0.77642 (6)0.0285 (2)
S60.59798 (6)0.22584 (14)0.88019 (6)0.0321 (2)
S260.00637 (5)0.77810 (14)0.62897 (6)0.0281 (2)
N10.48598 (16)0.5044 (4)0.84906 (18)0.0265 (7)
H10.46090.42810.80760.032*
N30.47771 (16)0.8030 (4)0.91970 (19)0.0258 (6)
N70.66257 (16)0.5891 (4)1.01923 (17)0.0238 (6)
H70.70040.49961.02770.029*
N90.59655 (16)0.8543 (4)1.03268 (18)0.0252 (6)
H90.58390.96731.05210.030*
N210.14076 (17)0.8882 (4)0.61649 (18)0.0250 (6)
H210.14910.91720.67100.030*
N230.19977 (16)0.8842 (4)0.49758 (18)0.0239 (6)
N270.00114 (16)0.7200 (4)0.42570 (17)0.0223 (6)
H270.04730.68760.43060.027*
N290.10400 (16)0.7714 (4)0.37104 (17)0.0238 (6)
H290.13440.77810.33380.029*
C20.4499 (2)0.6740 (5)0.8601 (2)0.0274 (8)
H20.40040.70250.82180.033*
C40.55008 (19)0.7493 (5)0.9677 (2)0.0221 (7)
C50.59081 (18)0.5804 (5)0.9593 (2)0.0207 (7)
C60.5592 (2)0.4381 (5)0.8969 (2)0.0244 (7)
C80.66458 (19)0.7552 (5)1.0615 (2)0.0263 (8)
H80.70780.79781.10570.032*
C220.2022 (2)0.9159 (5)0.5783 (2)0.0262 (8)
H220.25120.96210.61260.031*
C240.12665 (19)0.8192 (5)0.4555 (2)0.0208 (7)
C250.06210 (19)0.7868 (5)0.4905 (2)0.0208 (7)
C260.06553 (19)0.8180 (5)0.5776 (2)0.0216 (7)
C280.0278 (2)0.7130 (5)0.3550 (2)0.0263 (8)
H280.00260.67240.30090.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0183 (2)0.0318 (2)0.0238 (2)0.00040 (16)0.00371 (15)0.00279 (18)
Cl10.0256 (4)0.0327 (5)0.0237 (4)0.0028 (3)0.0028 (3)0.0016 (4)
Cl20.0213 (4)0.0329 (5)0.0277 (5)0.0026 (3)0.0043 (3)0.0056 (4)
Cl30.0189 (4)0.0365 (5)0.0366 (5)0.0019 (3)0.0035 (4)0.0123 (4)
Cl40.0224 (4)0.0381 (5)0.0254 (4)0.0039 (3)0.0059 (3)0.0010 (4)
S60.0323 (5)0.0271 (5)0.0374 (6)0.0008 (4)0.0091 (4)0.0047 (4)
S260.0294 (5)0.0320 (5)0.0255 (5)0.0036 (4)0.0113 (4)0.0005 (4)
N10.0203 (15)0.0323 (17)0.0257 (16)0.0027 (12)0.0025 (12)0.0077 (13)
N30.0184 (14)0.0300 (16)0.0274 (16)0.0016 (11)0.0017 (12)0.0017 (13)
N70.0185 (14)0.0274 (16)0.0233 (15)0.0029 (11)0.0002 (11)0.0016 (12)
N90.0210 (15)0.0256 (16)0.0275 (16)0.0028 (11)0.0020 (12)0.0025 (13)
N210.0279 (16)0.0316 (16)0.0158 (14)0.0023 (12)0.0056 (12)0.0018 (13)
N230.0197 (14)0.0274 (16)0.0245 (15)0.0012 (11)0.0045 (11)0.0019 (13)
N270.0163 (13)0.0260 (15)0.0238 (15)0.0017 (11)0.0030 (11)0.0010 (12)
N290.0213 (14)0.0297 (16)0.0210 (15)0.0009 (12)0.0062 (11)0.0007 (12)
C20.0163 (17)0.037 (2)0.0271 (19)0.0022 (14)0.0006 (14)0.0028 (16)
C40.0192 (16)0.0247 (18)0.0227 (18)0.0002 (13)0.0050 (13)0.0005 (14)
C50.0155 (16)0.0297 (19)0.0162 (16)0.0000 (12)0.0022 (12)0.0006 (14)
C60.0271 (18)0.0243 (18)0.0240 (18)0.0040 (13)0.0107 (14)0.0002 (14)
C80.0203 (17)0.0316 (19)0.0258 (19)0.0018 (14)0.0026 (14)0.0003 (16)
C220.0216 (17)0.0280 (19)0.0272 (19)0.0037 (14)0.0016 (14)0.0001 (15)
C240.0196 (16)0.0219 (17)0.0205 (17)0.0003 (12)0.0037 (13)0.0002 (14)
C250.0189 (16)0.0233 (17)0.0200 (17)0.0004 (12)0.0041 (13)0.0000 (14)
C260.0244 (17)0.0170 (16)0.0226 (17)0.0016 (12)0.0035 (14)0.0031 (13)
C280.0250 (18)0.0306 (19)0.0215 (18)0.0020 (14)0.0015 (14)0.0040 (15)
Geometric parameters (Å, º) top
Zn1—Cl12.2547 (9)N9—H90.8800
Zn1—Cl22.2776 (10)N21—C221.348 (4)
Zn1—Cl32.2750 (9)N21—C261.386 (4)
Zn1—Cl42.2861 (9)N21—H210.8800
S6—C61.647 (4)N23—C221.310 (4)
S26—C261.655 (3)N23—C241.359 (4)
N1—C21.347 (4)C24—C251.368 (4)
N1—C61.392 (4)N27—C251.378 (4)
N1—H10.8800N27—C281.321 (4)
N3—C21.313 (4)N27—H270.8800
N3—C41.357 (4)N29—C281.334 (4)
C4—C51.374 (4)N29—C241.368 (4)
C5—C61.418 (5)N29—H290.8800
N7—C51.383 (4)C2—H20.9500
N7—C81.323 (4)C8—H80.9500
N7—H70.8800C22—H220.9500
N9—C81.339 (4)C25—C261.408 (5)
N9—C41.368 (4)C28—H280.9500
Cl1—Zn1—Cl3109.44 (4)N1—C2—H2117.4
Cl1—Zn1—Cl2114.54 (4)N3—C4—N9126.4 (3)
Cl3—Zn1—Cl2110.12 (3)N3—C4—C5126.3 (3)
Cl1—Zn1—Cl4109.33 (3)N9—C4—C5107.3 (3)
Cl3—Zn1—Cl4107.60 (4)C4—C5—N7106.6 (3)
Cl2—Zn1—Cl4105.54 (4)C4—C5—C6121.8 (3)
C2—N1—C6126.2 (3)N7—C5—C6131.5 (3)
C2—N1—H1116.9N1—C6—C5108.8 (3)
C6—N1—H1116.9N1—C6—S6123.0 (3)
C2—N3—C4111.7 (3)C5—C6—S6128.2 (3)
C8—N7—C5108.2 (3)N7—C8—N9109.7 (3)
C8—N7—H7125.9N7—C8—H8125.1
C5—N7—H7125.9N9—C8—H8125.1
C8—N9—C4108.1 (3)N23—C22—N21125.2 (3)
C8—N9—H9126.0N23—C22—H22117.4
C4—N9—H9126.0N21—C22—H22117.4
C22—N21—C26125.8 (3)N23—C24—N29126.7 (3)
C22—N21—H21117.1N23—C24—C25126.0 (3)
C26—N21—H21117.1N29—C24—C25107.3 (3)
C22—N23—C24111.7 (3)C24—C25—N27106.7 (3)
C28—N27—C25108.3 (3)C24—C25—C26122.0 (3)
C28—N27—H27125.8N27—C25—C26131.3 (3)
C25—N27—H27125.8N21—C26—C25109.2 (3)
C28—N29—C24108.1 (3)N21—C26—S26123.6 (3)
C28—N29—H29125.9C25—C26—S26127.2 (3)
C24—N29—H29125.9N27—C28—N29109.6 (3)
N3—C2—N1125.1 (3)N27—C28—H28125.2
N3—C2—H2117.4N29—C28—H28125.2
C4—N3—C2—N12.6 (5)C24—N23—C22—N210.2 (5)
C6—N1—C2—N31.5 (6)C26—N21—C22—N231.4 (6)
C2—N3—C4—N9177.3 (3)C22—N23—C24—N29179.7 (3)
C2—N3—C4—C51.6 (5)C22—N23—C24—C250.6 (5)
C8—N9—C4—N3177.5 (3)C28—N29—C24—N23179.6 (3)
C8—N9—C4—C51.6 (4)C28—N29—C24—C250.4 (4)
N3—C4—C5—N7178.1 (3)N23—C24—C25—N27179.4 (3)
N9—C4—C5—N71.1 (4)N29—C24—C25—N270.2 (4)
N3—C4—C5—C60.5 (5)N23—C24—C25—C260.4 (5)
N9—C4—C5—C6179.7 (3)N29—C24—C25—C26178.7 (3)
C8—N7—C5—C40.1 (4)C28—N27—C25—C240.1 (4)
C8—N7—C5—C6178.5 (3)C28—N27—C25—C26178.9 (4)
C2—N1—C6—C50.8 (5)C22—N21—C26—C252.2 (5)
C2—N1—C6—S6178.6 (3)C22—N21—C26—S26177.3 (3)
C4—C5—C6—N11.7 (4)C24—C25—C26—N211.7 (4)
N7—C5—C6—N1176.6 (3)N27—C25—C26—N21179.7 (3)
C4—C5—C6—S6177.7 (3)C24—C25—C26—S26177.8 (3)
N7—C5—C6—S64.1 (6)N27—C25—C26—S260.8 (6)
C5—N7—C8—N91.0 (4)C25—N27—C28—N290.3 (4)
C4—N9—C8—N71.6 (4)C24—N29—C28—N270.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl30.882.343.180 (3)159
N21—H21···Cl20.882.763.245 (3)116
N7—H7···N23i0.882.012.811 (4)151
N9—H9···N3ii0.882.002.857 (4)163
N21—H21···Cl4iii0.882.453.216 (3)146
N27—H27···Cl1iv0.882.313.184 (3)174
N29—H29···Cl2v0.882.303.134 (3)159
C2—H2···Cl20.952.583.432 (3)149
C8—H8···Cl4vi0.952.613.540 (3)165
C28—H28···S26v0.952.783.556 (4)140
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+2, z+2; (iii) x, y+1, z; (iv) x, y+1, z+1; (v) x, y+3/2, z1/2; (vi) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formula(C5H5N4S)2[ZnCl4]
Mr513.55
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)17.1397 (5), 6.8500 (2), 16.1142 (5)
β (°) 103.021 (2)
V3)1843.27 (10)
Z4
Radiation typeMo Kα
µ (mm1)2.15
Crystal size (mm)0.25 × 0.15 × 0.15
Data collection
DiffractometerBruker Kappa APEX-II
diffractometer
Absorption correctionMulti-scan
(MULABS in PLATON; Blessing, 1995; Spek, 2003)
Tmin, Tmax0.603, 0.724
No. of measured, independent and
observed [I > 2σ(I)] reflections
27322, 4528, 3408
Rint0.087
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.084, 1.05
No. of reflections4528
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.44

Computer programs: Collect (Bruker, 2004), DENZO–SMN (Otwinowski & Minor, 1997), DENZO–SMN, SIR2002 (Burla, et al., 2003), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
Zn1—Cl12.2547 (9)N7—C81.323 (4)
Zn1—Cl22.2776 (10)N9—C81.339 (4)
Zn1—Cl32.2750 (9)N9—C41.368 (4)
Zn1—Cl42.2861 (9)C24—C251.368 (4)
S6—C61.647 (4)N27—C251.378 (4)
S26—C261.655 (3)N27—C281.321 (4)
C4—C51.374 (4)N29—C281.334 (4)
N7—C51.383 (4)N29—C241.368 (4)
Cl1—Zn1—Cl3109.44 (4)Cl1—Zn1—Cl4109.33 (3)
Cl1—Zn1—Cl2114.54 (4)Cl3—Zn1—Cl4107.60 (4)
Cl3—Zn1—Cl2110.12 (3)Cl2—Zn1—Cl4105.54 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl30.882.343.180 (3)158.7
N21—H21···Cl20.882.763.245 (3)116.2
N7—H7···N23i0.882.012.811 (4)150.9
N9—H9···N3ii0.882.002.857 (4)162.9
N21—H21···Cl4iii0.882.453.216 (3)145.8
N27—H27···Cl1iv0.882.313.184 (3)174.4
N29—H29···Cl2v0.882.303.134 (3)158.6
C2—H2···Cl20.952.583.432 (3)148.6
C8—H8···Cl4vi0.952.613.540 (3)164.8
C28—H28···S26v0.952.783.556 (4)139.8
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+2, z+2; (iii) x, y+1, z; (iv) x, y+1, z+1; (v) x, y+3/2, z1/2; (vi) x+1, y+1, z+2.
 

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