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In the crystal structure of the title compound, [N,N′-bis(3-­amino­propyl)­ethyl­enedi­amine-κ4N,N′,N′′,N′′′][1,3,5-triazine-2,4,6(1H,3H,5H)-tri­thionato(2−)-κ2N,S]­zinc(II) ethanol sol­vate, [Zn(C8H22N4)2(C3HN3S3)]·C2H6O, the ZnII atom is octa­hedrally coordinated by four N atoms [Zn—N = 2.104 (2)–2.203 (2) Å] of a tetradentate N-donor N,N′-bis(3-­amino­propyl)­ethyl­enedi­amine (bapen) ligand and by two S and N atoms [Zn—S = 2.5700 (7) Å and Zn—N = 2.313 (2) Å] of a tri­thio­cyanurate(2−) (ttcH2−) dianion bonded as a bidentate ligand in a cis configuration. The crystal structure of the compound is stabilized by a network of hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103025836/gd1284sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103025836/gd1284Isup2.hkl
Contains datablock I

CCDC reference: 229088

Comment top

Trithiocyanuric acid (2,4,6-trimercaptotriazine, ttcH3) and its trisodium salt have a very wide range of applications, e.g. they can be used as precipitating agents for heavy metals (Henke et al., 2000; Matlock et al., 2001, 2002). The acid also shows antitoxoplasmal activity and is more effective than the presently used drugs 5-fluorouracil and emimicin (Iltzsch & Tankersley, 1994). The formation of metal complexes with trithiocyanuric acid depends strongly on the pH value. At pH below 5, only ttcH3 exists, which is insoluble in water, while ttcH2, ttcH2− and ttc3− anions are formed if the pH is increased. In connection with the extent of ttcH3 deprotonation, the manner of coordination of the anion to the metal centre can be different and transition metal complexes with various nuclearities can be formed. These complexes can be mononuclear (Mahon et al., 2003; Zhao et al., 2000; Kopel et al., 1998, 2001, 2003; Kopel, Trávníček, Panchártková et al., 1999; Kopel, Trávníček, Kvítek et al., 1999), binuclear (Yamanari et al., 1993), trinuclear (Ainscough et al., 1993; Hunks et al., 1999; Haiduc et al., 2001; Cecconi et al., 2002) or even polynuclear (Chan et al., 1996; Tzeng et al., 1997; Aoki, Shiro & Kimura, 2002; Aoki, Zulkefeli et al., 2002). Here, we report the preparation and crystal structure of the title mononuclear [Zn(bapen)(ttcH)]·EtOH complex, (I) [bapen is N,N'-bis(3-aminopropyl)ethylenediamine]. \sch

The structure of the title ZnII complex, (I), is very similar to that previously reported for [Ni(bapen)(ttcH)]·2H2O, (II) (Kopel, Trávníček, Kvítek et al., 1999). Complex (II) is octahedral, with Ni—N(bapen) bond lengths in the range 2.08–2.12 Å, while the Ni—N and Ni—S (ttcH2−) distances are 2.143 and 2.521 Å, respectively. These interatomic parameters differ significantly from those found for (I). It is necessary to emphasize that the structure of (I) represents the first known example of a mononuclear ZnII complex with a coordinated trithiocyanurate dianion. If we compare (I) with known ZnII trithiocyanurate clusters (Aoki, Shiro & Kimura, 2002; Aoki, Zulkefeli et al., 2002), we can note that the higher nuclearity of the latter complexes was caused by the total deprotonation of ttcH3 as well as by the use of suitable bridging ligands. To prevent the formation of a polynuclear complex, we have used the bapen ligand for the synthesis of (I).

The crystal structure of (I) consists of [Zn(bapen)(ttcH)] and ethanol molecules (Fig. 1). The ZnII ion in the complex adopts a substantially distorted octahedral geometry, defined by the four N atoms of the bapen ligand and two S and N atoms of the ttcH2− anion in a cis configuration. The bapen ligand is bonded as a tetradentate N-donor ligand and forms with the Zn atom a five-membered (ring B) and two six-membered (ring A, containing atoms N1 and N2, and ring C, containing atoms N4 and N3) rings. The Zn—N distances in these rings (2.10–2.20 Å) are comparable with the average length (2.16 Å) of this bond in related complexes in the Cambridge Structural Database (Version 5.24.3; Allen, 2002). The five-membered ring B is twisted and both six-membered rings A and C are in chair conformations. The Cremer-Pople puckering parameters (Cremer & Pople, 1975) are Q = 0.563 (3) Å, θ = 161.5 (2)° and ϕ2 = −18.8 (8)° for ring A, Q = 0.575 (3) Å, θ = 165.1 (2)° and ϕ2 = −5.7 (9)° for ring C, and q2 = 0.458 (2) Å and ϕ2 = −64.8 (3)° for ring B.

The coordination of the ttcH2− anion to Zn in (I) differs significantly from the recently reported polynuclear ZnII trithiocyanurate structure (Aoki, Zulkefeli et al., 2002). While two distinct average values for the Zn—S (2.30 and 2.88 Å) and Zn—N (3.06 and 2.07 Å) bond distances for two different Zn-ttc coordination modes in Aoki's structure show the coordination of ttc through either S or N atoms, the intermediate values of the Zn—S (2.570 Å) and Zn—N (2.313 Å) bond distances in (I) indicate that the ttcH2− is chelated as a bidentate ligand.

In the crystal lattice of (I), Zn complex molecules and molecules of ethanol are linked by a network of hydrogen bonds (Table 2). The shortest one (N—H.·N 2.09 Å) connects atoms N4 and N6i from inversion-related molecules [symmetry code: (i) 1 − x, −y, 1 − z].

Experimental top

N,N'-Bis(3-aminopropyl)ethylenediamine (0.18 ml, 1 mmol) was added to an ethanolic solution (80 ml) of zinc acetate dihydrate (0.22 g, 1 mmol) with stirring at room temperature. Into this solution, the trisodium salt of trithiocyanuric acid nonahydrate (ttcNa3·9H2O) (0.4 g, 1 mmol), dissolved in water (5 ml), was added with stirring over a period of 30 min. The colour of the solution changed to light yellow and a small amount of white precipitate formed. The precipitate was filtered off and discarded and the filtrate was left to crystallize at room temperature. Light-yellow crystals of (I) were obtained after a week. These were filtered off, washed with a small amount of ethanol and dried in the air. Elemental analysis (EA1108 CHNS Analyzer, Fisons Instruments, Beverly, Massachusetts, USA), found: C 33.3, H 6.1, N 21.2, S 21.0%; calculated: C 33.9, H 6.3, N 21.3, S 20.9%.

Refinement top

H atoms attached to C and N atoms were positioned geometrically, with C—H distances of 0.99 Å and N—H distances in the range 0.88–0.93 Å, and with Uiso values derived from Ueq of the corresponding C or N atoms. The parameters of atom H1O attached to atom O1 were refined with the O···H distance restrained to 0.95 (2) Å.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres at arbitrary radii.
[N,N'-bis(3-aminopropyl)ethylenediamine-κ4N,N',N'',N'''][1,3,5-triazine- 2,4,6(1H,3H,5H)-trithioneκ2N,S]zinc(II) ethanol solvate top
Crystal data top
[Zn(C8H22N4)(C3HN3S3)]·C2H6OZ = 2
Mr = 460.98F(000) = 484
Triclinic, P1Dx = 1.505 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0791 (14) ÅCell parameters from 2410 reflections
b = 11.0455 (15) Åθ = 26.5–2.2°
c = 11.3580 (11) ŵ = 1.53 mm1
α = 93.592 (10)°T = 120 K
β = 102.316 (11)°Prism, light yellow
γ = 112.167 (14)°0.40 × 0.40 × 0.40 mm
V = 1017.6 (3) Å3
Data collection top
Kuma KM4 with CCD area detector
diffractometer
4279 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Enhance (Oxford Diffraction) monochromatorθmax = 28.4°, θmin = 2.5°
Detector resolution: 16.3 pixels mm-1h = 1111
rotation method, ω scank = 1314
6681 measured reflectionsl = 1514
4458 independent 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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.055P)2 + 1.75P]
where P = (Fo2 + 2Fc2)/3
4458 reflections(Δ/σ)max = 0.001
230 parametersΔρmax = 1.08 e Å3
0 restraintsΔρmin = 0.66 e Å3
Crystal data top
[Zn(C8H22N4)(C3HN3S3)]·C2H6Oγ = 112.167 (14)°
Mr = 460.98V = 1017.6 (3) Å3
Triclinic, P1Z = 2
a = 9.0791 (14) ÅMo Kα radiation
b = 11.0455 (15) ŵ = 1.53 mm1
c = 11.3580 (11) ÅT = 120 K
α = 93.592 (10)°0.40 × 0.40 × 0.40 mm
β = 102.316 (11)°
Data collection top
Kuma KM4 with CCD area detector
diffractometer
4279 reflections with I > 2σ(I)
6681 measured reflectionsRint = 0.023
4458 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 1.08 e Å3
4458 reflectionsΔρmin = 0.66 e Å3
230 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
Zn0.44691 (3)0.21844 (2)0.69155 (2)0.01459 (9)
S10.31572 (7)0.06521 (5)0.48436 (5)0.01884 (13)
S20.85613 (7)0.50263 (6)0.62917 (5)0.02149 (13)
S30.73699 (7)0.20877 (6)0.20745 (5)0.02066 (13)
N10.2868 (2)0.11116 (19)0.79283 (18)0.0182 (4)
H1A0.29820.03240.79970.022*
H1B0.31980.15820.87030.022*
N20.3020 (2)0.3349 (2)0.63181 (18)0.0191 (4)
H20.31300.34940.55380.023*
N30.5945 (2)0.39975 (17)0.81964 (16)0.0143 (3)
H30.66910.45430.78110.017*
N40.6261 (2)0.14065 (18)0.75268 (18)0.0175 (4)
H4A0.57490.04990.73320.021*
H4B0.70320.16860.70830.021*
N50.5826 (2)0.28271 (18)0.54067 (17)0.0154 (4)
N60.5283 (2)0.14832 (18)0.34803 (17)0.0175 (4)
N70.7781 (2)0.33083 (18)0.42804 (17)0.0151 (3)
H70.87870.37750.42290.018*
C10.1092 (3)0.0811 (2)0.7426 (2)0.0252 (5)
H1C0.04630.03140.79780.030*
H1D0.06970.02360.66220.030*
C20.0754 (3)0.2048 (3)0.7274 (2)0.0253 (5)
H2A0.04340.18120.71890.030*
H2B0.13650.27020.80280.030*
C30.1217 (3)0.2701 (3)0.6193 (2)0.0258 (5)
H3A0.07090.20220.54500.031*
H3B0.07460.33730.60750.031*
C40.3832 (3)0.4676 (2)0.7085 (2)0.0225 (5)
H4C0.29850.50070.71850.027*
H4D0.45760.53000.66690.027*
C50.4817 (3)0.4636 (2)0.8340 (2)0.0187 (4)
H5A0.54550.55480.87900.022*
H5B0.40590.41340.88150.022*
C60.6916 (3)0.3923 (2)0.9390 (2)0.0176 (4)
H6A0.61550.34460.98730.021*
H6B0.75870.48310.98390.021*
C70.8049 (3)0.3221 (2)0.9270 (2)0.0193 (4)
H7A0.88320.33741.00730.023*
H7B0.86970.36220.86900.023*
C80.7150 (3)0.1731 (2)0.8832 (2)0.0203 (4)
H8A0.79570.13190.89680.024*
H8B0.63560.13480.93220.024*
C90.4900 (3)0.1734 (2)0.4534 (2)0.0161 (4)
C100.6752 (3)0.2278 (2)0.33580 (19)0.0151 (4)
C110.7298 (3)0.3637 (2)0.5281 (2)0.0153 (4)
O10.3590 (2)0.1850 (2)1.06990 (17)0.0285 (4)
C130.1115 (4)0.2027 (4)1.0840 (4)0.0501 (9)
H13A0.14840.28421.04850.075*
H13B0.04690.21071.14080.075*
H13C0.04320.12761.01880.075*
C120.2555 (4)0.1812 (3)1.1500 (3)0.0422 (8)
H12A0.31750.25091.22230.051*
H12B0.21920.09421.17830.051*
H1O0.451 (4)0.180 (4)1.121 (3)0.060 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.01375 (14)0.01480 (14)0.01548 (15)0.00543 (10)0.00536 (10)0.00039 (9)
S10.0150 (3)0.0170 (3)0.0197 (3)0.0001 (2)0.0081 (2)0.00146 (19)
S20.0195 (3)0.0182 (3)0.0190 (3)0.0028 (2)0.0102 (2)0.0027 (2)
S30.0265 (3)0.0195 (3)0.0181 (3)0.0076 (2)0.0133 (2)0.0026 (2)
N10.0157 (9)0.0164 (9)0.0210 (10)0.0037 (7)0.0066 (7)0.0023 (7)
N20.0191 (9)0.0228 (9)0.0182 (9)0.0102 (8)0.0069 (7)0.0041 (7)
N30.0151 (8)0.0133 (8)0.0157 (9)0.0051 (7)0.0072 (7)0.0032 (6)
N40.0169 (9)0.0157 (8)0.0210 (10)0.0069 (7)0.0070 (7)0.0009 (7)
N50.0152 (9)0.0144 (8)0.0159 (9)0.0031 (7)0.0077 (7)0.0017 (7)
N60.0195 (9)0.0153 (8)0.0173 (9)0.0048 (7)0.0083 (7)0.0008 (7)
N70.0141 (8)0.0150 (8)0.0162 (9)0.0035 (7)0.0081 (7)0.0035 (7)
C10.0142 (10)0.0241 (11)0.0331 (13)0.0019 (9)0.0087 (9)0.0046 (10)
C20.0157 (10)0.0292 (12)0.0314 (13)0.0084 (9)0.0087 (9)0.0030 (10)
C30.0171 (11)0.0332 (13)0.0276 (13)0.0127 (10)0.0023 (9)0.0034 (10)
C40.0275 (12)0.0177 (10)0.0259 (12)0.0124 (9)0.0075 (10)0.0058 (9)
C50.0218 (11)0.0165 (10)0.0204 (11)0.0094 (8)0.0083 (9)0.0018 (8)
C60.0179 (10)0.0155 (10)0.0170 (10)0.0042 (8)0.0045 (8)0.0003 (8)
C70.0165 (10)0.0193 (10)0.0195 (11)0.0053 (8)0.0031 (8)0.0013 (8)
C80.0228 (11)0.0170 (10)0.0211 (11)0.0089 (9)0.0043 (9)0.0022 (8)
C90.0147 (10)0.0147 (9)0.0187 (10)0.0049 (8)0.0063 (8)0.0022 (8)
C100.0195 (10)0.0138 (9)0.0153 (10)0.0077 (8)0.0084 (8)0.0046 (7)
C110.0158 (10)0.0144 (9)0.0167 (10)0.0050 (8)0.0081 (8)0.0044 (7)
O10.0236 (9)0.0372 (10)0.0262 (9)0.0132 (8)0.0078 (7)0.0035 (8)
C130.0412 (18)0.056 (2)0.069 (2)0.0266 (16)0.0271 (17)0.0318 (19)
C120.0389 (17)0.0464 (18)0.057 (2)0.0230 (14)0.0272 (15)0.0307 (16)
Geometric parameters (Å, º) top
Zn—N12.104 (2)C1—H1C0.9900
Zn—N42.1249 (19)C1—H1D0.9900
Zn—N32.1682 (19)C2—C31.520 (4)
Zn—N22.2031 (19)C2—H2A0.9900
Zn—N52.3132 (18)C2—H2B0.9900
Zn—S12.5700 (7)C3—H3A0.9900
S1—C91.708 (2)C3—H3B0.9900
S2—C111.697 (2)C4—C51.525 (3)
S3—C101.698 (2)C4—H4C0.9900
N1—C11.488 (3)C4—H4D0.9900
N1—H1A0.9200C5—H5A0.9900
N1—H1B0.9200C5—H5B0.9900
N2—C41.484 (3)C6—C71.526 (3)
N2—C31.488 (3)C6—H6A0.9900
N2—H20.9300C6—H6B0.9900
N3—C51.475 (3)C7—C81.527 (3)
N3—C61.476 (3)C7—H7A0.9900
N3—H30.9300C7—H7B0.9900
N4—C81.477 (3)C8—H8A0.9900
N4—H4A0.9200C8—H8B0.9900
N4—H4B0.9200O1—C121.432 (4)
N5—C111.343 (3)O1—H1O0.93 (4)
N5—C91.370 (3)C13—C121.472 (5)
N6—C101.334 (3)C13—H13A0.9800
N6—C91.355 (3)C13—H13B0.9800
N7—C111.377 (3)C13—H13C0.9800
N7—C101.377 (3)C12—H12A0.9900
N7—H70.8800C12—H12B0.9900
C1—C21.521 (4)
N1—Zn—N494.66 (8)N2—C3—C2114.4 (2)
N1—Zn—N3100.92 (7)N2—C3—H3A108.6
N4—Zn—N390.46 (7)C2—C3—H3A108.6
N1—Zn—N293.77 (8)N2—C3—H3B108.6
N4—Zn—N2169.06 (8)C2—C3—H3B108.6
N3—Zn—N281.09 (7)H3A—C3—H3B107.6
N1—Zn—N5163.89 (7)N2—C4—C5111.68 (18)
N4—Zn—N584.67 (7)N2—C4—H4C109.3
N3—Zn—N595.18 (7)C5—C4—H4C109.3
N2—Zn—N589.15 (7)N2—C4—H4D109.3
N1—Zn—S199.81 (6)C5—C4—H4D109.3
N4—Zn—S195.51 (5)H4C—C4—H4D107.9
N3—Zn—S1157.87 (5)N3—C5—C4109.54 (18)
N2—Zn—S189.91 (6)N3—C5—H5A109.8
N5—Zn—S164.32 (5)C4—C5—H5A109.8
C9—S1—Zn80.99 (8)N3—C5—H5B109.8
C1—N1—Zn116.11 (15)C4—C5—H5B109.8
C1—N1—H1A108.3H5A—C5—H5B108.2
Zn—N1—H1A108.3N3—C6—C7112.71 (18)
C1—N1—H1B108.3N3—C6—H6A109.1
Zn—N1—H1B108.3C7—C6—H6A109.1
H1A—N1—H1B107.4N3—C6—H6B109.1
C4—N2—C3113.98 (19)C7—C6—H6B109.1
C4—N2—Zn108.50 (14)H6A—C6—H6B107.8
C3—N2—Zn116.68 (15)C6—C7—C8114.09 (19)
C4—N2—H2105.6C6—C7—H7A108.7
C3—N2—H2105.6C8—C7—H7A108.7
Zn—N2—H2105.6C6—C7—H7B108.7
C5—N3—C6111.55 (17)C8—C7—H7B108.7
C5—N3—Zn105.99 (13)H7A—C7—H7B107.6
C6—N3—Zn118.77 (13)N4—C8—C7112.60 (19)
C5—N3—H3106.6N4—C8—H8A109.1
C6—N3—H3106.6C7—C8—H8A109.1
Zn—N3—H3106.6N4—C8—H8B109.1
C8—N4—Zn118.67 (14)C7—C8—H8B109.1
C8—N4—H4A107.6H8A—C8—H8B107.8
Zn—N4—H4A107.6N6—C9—N5124.5 (2)
C8—N4—H4B107.6N6—C9—S1120.12 (16)
Zn—N4—H4B107.6N5—C9—S1115.42 (16)
H4A—N4—H4B107.1N6—C10—N7119.33 (19)
C11—N5—C9118.13 (19)N6—C10—S3121.87 (17)
C11—N5—Zn140.07 (15)N7—C10—S3118.77 (17)
C9—N5—Zn98.37 (13)N5—C11—N7117.62 (19)
C10—N6—C9117.14 (19)N5—C11—S2122.90 (17)
C11—N7—C10122.54 (18)N7—C11—S2119.48 (16)
C11—N7—H7118.7C12—O1—H1O103 (3)
C10—N7—H7118.7C12—C13—H13A109.5
N1—C1—C2112.9 (2)C12—C13—H13B109.5
N1—C1—H1C109.0H13A—C13—H13B109.5
C2—C1—H1C109.0C12—C13—H13C109.5
N1—C1—H1D109.0H13A—C13—H13C109.5
C2—C1—H1D109.0H13B—C13—H13C109.5
H1C—C1—H1D107.8O1—C12—C13109.1 (3)
C3—C2—C1115.1 (2)O1—C12—H12A109.9
C3—C2—H2A108.5C13—C12—H12A109.9
C1—C2—H2A108.5O1—C12—H12B109.9
C3—C2—H2B108.5C13—C12—H12B109.9
C1—C2—H2B108.5H12A—C12—H12B108.3
H2A—C2—H2B107.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O10.922.203.065 (3)156
N1—H1A···S3i0.922.553.458 (2)167
N3—H3···S20.932.613.475 (2)154
N4—H4A···N6i0.922.092.991 (3)167
N7—H7···S2ii0.882.493.361 (2)170
O1—H1O···S3iii0.93 (4)2.46 (4)3.357 (2)161 (3)
O1—H1O···N6iii0.93 (4)2.61 (3)3.326 (3)135 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z+1; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Zn(C8H22N4)(C3HN3S3)]·C2H6O
Mr460.98
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)9.0791 (14), 11.0455 (15), 11.3580 (11)
α, β, γ (°)93.592 (10), 102.316 (11), 112.167 (14)
V3)1017.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.53
Crystal size (mm)0.40 × 0.40 × 0.40
Data collection
DiffractometerKuma KM4 with CCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6681, 4458, 4279
Rint0.023
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.097, 1.01
No. of reflections4458
No. of parameters230
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.08, 0.66

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), CrysAlis RED, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPIII (Johnson & Burnett, 1996), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
Zn—N12.104 (2)Zn—S12.5700 (7)
Zn—N42.1249 (19)S1—C91.708 (2)
Zn—N32.1682 (19)S2—C111.697 (2)
Zn—N22.2031 (19)S3—C101.698 (2)
Zn—N52.3132 (18)
N1—Zn—N494.66 (8)N2—Zn—S189.91 (6)
N1—Zn—N3100.92 (7)N5—Zn—S164.32 (5)
N4—Zn—N390.46 (7)C9—S1—Zn80.99 (8)
N1—Zn—N293.77 (8)C1—N1—Zn116.11 (15)
N4—Zn—N2169.06 (8)N6—C9—N5124.5 (2)
N3—Zn—N281.09 (7)N6—C9—S1120.12 (16)
N1—Zn—N5163.89 (7)N5—C9—S1115.42 (16)
N4—Zn—N584.67 (7)N6—C10—N7119.33 (19)
N3—Zn—N595.18 (7)N6—C10—S3121.87 (17)
N2—Zn—N589.15 (7)N7—C10—S3118.77 (17)
N1—Zn—S199.81 (6)N5—C11—N7117.62 (19)
N4—Zn—S195.51 (5)N5—C11—S2122.90 (17)
N3—Zn—S1157.87 (5)N7—C11—S2119.48 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O10.922.203.065 (3)156
N1—H1A···S3i0.922.553.458 (2)167
N3—H3···S20.932.613.475 (2)154
N4—H4A···N6i0.922.092.991 (3)167
N7—H7···S2ii0.882.493.361 (2)170
O1—H1O···S3iii0.93 (4)2.46 (4)3.357 (2)161 (3)
O1—H1O···N6iii0.93 (4)2.61 (3)3.326 (3)135 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z+1; (iii) x, y, z+1.
 

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