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Acta Cryst. (2009). E65, m549    [ doi:10.1107/S1600536809013385 ]

Bis([mu]-4-hydroxy-2-oxidobenzaldehyde 4-ethylthiosemicarbazone)-[kappa]4O2,N1,S:O2;[kappa]4O2:O2,N1,S-bis[chloridozinc(II)] dimethyl sulfoxide trisolvate

K. W. Tan, C. H. Ng, M. J. Maah and S. W. Ng

Abstract top

The two ZnII atoms in the title compound, [Zn2(C10H12N3O2S)2Cl2]·3C2H6OS, are each N,O,S-chelated by a mono-deprotonated Schiff base ligand. The Zn atoms are bridged through the phenolate O atom, leading to a central Zn2O2 core. Each Zn atom has a Cl atom in the apical position of a distorted square-pyramidal environment. Hydroxy-DMSO (DMSO is dimethyl sulfoxide) O-H...O and amide-DMSO N-H...O hydrogen bonds link the components of the crystal structure. Two of the DMSO molecules are partially disordered, with each modelled over two sites of equal weight.

Related literature top

For (4-hydroxy-2-oxidobenzaldehyde thiosemicarbazonato)(phenanthroline)zinc DMSO monohydrate, see: Tan et al. (2009).

Experimental top

Zinc chloride (0.14 g, 1 mmol) and 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone (0.24 g, 1 mmol) were heated in ethanol (20 ml) for 3 h. The compound that separated on cooling the solution was recrystallized from a mixture of ethanol and DMSO.

Refinement top

Hydrogen atoms were placed in calculated positions (C–H 0.95 - 0.99 Å, N–H 0.88 Å, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C,N,O).

Two of the three DMSO molecules are disordered. For one of them, only the S5 atom is disordered; the occupancy could not be refined, and was arbitrarily assumed to be 50:50. Pairs of bond lengths involving the unprimed and primed atoms were restrained to within 0.01 Å of each other. The anisotropic displacement factors of the S5 and S5' atoms were restrained to be nearly isotropic. For the other DMSO molecule, only one of the methyl (C23) groups is disordered; the occupancy was also assumed to be 50:50. The two S–C bond lengths involving the unprimed and primed atoms was restrained to within 0.01 Å of each other; their anisotropic displacement factors were similarly restrained.

The final difference Fourier map had peaks/holes in the vicinity of the disordered DMSO.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid (Barbour, 2001) plot of Zn2Cl2(C10H12O2N3S)2.3DMSO at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii. The disorder is not shown.
Bis(µ-4-hydroxy-2-oxidobenzaldehyde 4-ethylthiosemicarbazone)-κ4O2,N1,S:O2; κ4O2:O2,N1,S-bis[chloridozinc(II)] dimethyl sulfoxide trisolvate top
Crystal data top
[Zn2(C10H12N3O2S)2Cl2]·3C2H6OSZ = 2
Mr = 912.60F(000) = 940
Triclinic, P1Dx = 1.595 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4151 (1) ÅCell parameters from 9909 reflections
b = 12.4349 (2) Åθ = 2.4–28.3°
c = 17.2423 (2) ŵ = 1.73 mm−1
α = 71.4438 (6)°T = 123 K
β = 89.7703 (7)°Block, yellow
γ = 83.4964 (6)°0.25 × 0.20 × 0.20 mm
V = 1900.30 (4) Å3
Data collection top
Bruker SMART APEX
diffractometer		8627 independent reflections
Radiation source: fine-focus sealed tube7501 reflections with I > 2σ(I)
graphiteRint = 0.027
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→11
Tmin = 0.672, Tmax = 0.724k = −16→16
17632 measured reflectionsl = −22→22
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0908P)2 + 2.245P]
where P = (Fo2 + 2Fc2)/3
8627 reflections(Δ/σ)max = 0.001
450 parametersΔρmax = 1.70 e Å−3
16 restraintsΔρmin = −1.03 e Å−3
Crystal data top
[Zn2(C10H12N3O2S)2Cl2]·3C2H6OSγ = 83.4964 (6)°
Mr = 912.60V = 1900.30 (4) Å3
Triclinic, P1Z = 2
a = 9.4151 (1) ÅMo Kα radiation
b = 12.4349 (2) ŵ = 1.73 mm−1
c = 17.2423 (2) ÅT = 123 K
α = 71.4438 (6)°0.25 × 0.20 × 0.20 mm
β = 89.7703 (7)°
Data collection top
Bruker SMART APEX
diffractometer		8627 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7501 reflections with I > 2σ(I)
Tmin = 0.672, Tmax = 0.724Rint = 0.027
17632 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.134Δρmax = 1.70 e Å−3
S = 1.00Δρmin = −1.03 e Å−3
8627 reflectionsAbsolute structure: ?
450 parametersFlack parameter: ?
16 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.58610 (3)0.43998 (3)0.218131 (19)0.01686 (10)
Zn20.56211 (3)0.18354 (3)0.330117 (19)0.01624 (10)
Cl10.79752 (8)0.47941 (7)0.15762 (5)0.03056 (18)
Cl20.76783 (7)0.05619 (6)0.36638 (4)0.02085 (15)
S10.37411 (8)0.07401 (7)0.31152 (5)0.02404 (17)
S20.48125 (9)0.61073 (6)0.24461 (5)0.02341 (17)
S30.92908 (8)0.61170 (6)0.65079 (5)0.02227 (16)
S40.89013 (10)−0.16673 (8)0.24447 (6)0.0391 (2)
S50.0006 (4)0.7784 (2)−0.0444 (2)0.0395 (9)0.50
S5'0.0124 (4)0.7539 (5)−0.0416 (2)0.0841 (18)0.50
O10.6071 (2)0.33696 (17)0.33727 (12)0.0182 (4)
O20.8161 (3)0.5768 (2)0.45489 (14)0.0267 (5)
H2O0.83650.58300.50050.040*
O30.5635 (2)0.28127 (17)0.21268 (12)0.0207 (4)
O40.6197 (3)0.0056 (2)0.07303 (16)0.0356 (6)
H4O0.6906−0.01980.10570.053*
O50.8326 (3)0.6623 (2)0.57495 (15)0.0300 (5)
O60.8582 (3)−0.0784 (2)0.16274 (17)0.0405 (6)
O70.1471 (4)0.7433 (3)0.0036 (2)0.0551 (8)
N10.4572 (3)0.1703 (2)0.44030 (15)0.0171 (5)
N20.3612 (3)0.0906 (2)0.46242 (15)0.0189 (5)
H2N0.33060.06990.51270.023*
N30.2167 (3)−0.0284 (2)0.43583 (16)0.0213 (5)
H3N0.1898−0.04080.48660.026*
N40.4198 (3)0.4913 (2)0.12552 (15)0.0186 (5)
N50.3484 (3)0.5999 (2)0.11010 (16)0.0218 (5)
H5N0.28870.62910.06750.026*
N60.2969 (3)0.7645 (2)0.13923 (17)0.0278 (6)
H6N0.23230.78300.09900.033*
C10.6292 (3)0.3671 (2)0.40342 (17)0.0160 (5)
C20.7112 (3)0.4557 (2)0.39834 (17)0.0182 (5)
H20.75080.49350.34750.022*
C30.7364 (3)0.4899 (2)0.46583 (18)0.0196 (6)
C40.6767 (3)0.4364 (3)0.54145 (18)0.0207 (6)
H40.69290.45960.58780.025*
C50.5945 (3)0.3498 (3)0.54691 (18)0.0203 (6)
H50.55290.31450.59760.024*
C60.5696 (3)0.3117 (2)0.48008 (17)0.0171 (5)
C70.4784 (3)0.2226 (2)0.49227 (17)0.0189 (5)
H70.43020.20060.54240.023*
C80.3138 (3)0.0440 (2)0.40855 (18)0.0182 (5)
C90.1519 (3)−0.0886 (3)0.38711 (19)0.0247 (6)
H9A0.2275−0.12690.36170.030*
H9B0.0891−0.03340.34290.030*
C100.0654 (3)−0.1763 (3)0.4423 (2)0.0273 (7)
H10A0.1287−0.23190.48490.041*
H10B0.0200−0.21570.40980.041*
H10C−0.0084−0.13800.46780.041*
C110.5363 (3)0.2507 (2)0.14728 (17)0.0184 (5)
C120.5907 (3)0.1422 (3)0.14537 (18)0.0221 (6)
H120.64710.09120.19050.027*
C130.5629 (4)0.1082 (3)0.07780 (19)0.0241 (6)
C140.4744 (4)0.1794 (3)0.01244 (19)0.0239 (6)
H140.45150.1542−0.03210.029*
C150.4212 (3)0.2864 (3)0.01366 (18)0.0224 (6)
H150.36180.3352−0.03100.027*
C160.4522 (3)0.3261 (2)0.07932 (17)0.0188 (5)
C170.3931 (3)0.4403 (3)0.07340 (17)0.0200 (6)
H170.33010.48120.02810.024*
C180.3696 (3)0.6611 (3)0.15971 (18)0.0208 (6)
C190.3170 (5)0.8499 (3)0.1791 (2)0.0385 (9)
H19A0.42000.85850.18170.046*
H19B0.28310.82430.23570.046*
C200.2352 (4)0.9629 (3)0.1322 (3)0.0398 (9)
H20A0.27050.98900.07650.060*
H20B0.24861.01910.15970.060*
H20C0.13330.95430.12970.060*
C211.0107 (4)0.7267 (3)0.6644 (2)0.0279 (7)
H21A1.07850.75220.62090.042*
H21B1.06170.70120.71780.042*
H21C0.93700.79010.66200.042*
C220.8139 (4)0.5914 (4)0.7354 (2)0.0411 (9)
H22A0.76110.66490.73330.062*
H22B0.87110.55990.78660.062*
H22C0.74620.53830.73260.062*
C230.9021 (12)−0.2911 (7)0.2100 (7)0.053 (2)*0.50
H23A0.8239−0.28190.17020.079*0.50
H23B0.8949−0.35970.25700.079*0.50
H23C0.9940−0.29890.18420.079*0.50
C23'0.9473 (10)−0.3045 (6)0.2467 (6)0.047 (2)*0.50
H23D0.8886−0.32490.20790.070*0.50
H23E0.9382−0.35720.30200.070*0.50
H23F1.0476−0.30960.23140.070*0.50
C240.7265 (5)−0.1906 (3)0.2938 (2)0.0384 (8)
H24A0.6874−0.12230.30700.058*
H24B0.7426−0.25560.34440.058*
H24C0.6585−0.20730.25750.058*
C25−0.0562 (7)0.6467 (6)−0.0429 (4)0.0777 (18)0.50
H25A−0.08710.60670.01200.117*0.50
H25B0.02330.5995−0.05740.117*0.50
H25C−0.13610.6611−0.08260.117*0.50
C260.0451 (5)0.8189 (4)−0.1478 (2)0.0421 (9)0.50
H26A0.08540.8917−0.16250.063*0.50
H26B−0.04110.8273−0.18200.063*0.50
H26C0.11570.7601−0.15680.063*0.50
C25'−0.0562 (7)0.6467 (6)−0.0429 (4)0.0777 (18)0.50
H25D−0.06360.59630.01330.117*0.50
H25E0.00370.6059−0.07370.117*0.50
H25F−0.15180.6702−0.06920.117*0.50
C26'0.0451 (5)0.8189 (4)−0.1478 (2)0.0421 (9)0.50
H26D0.11870.8703−0.15330.063*0.50
H26E−0.04350.8624−0.17630.063*0.50
H26F0.07780.7594−0.17210.063*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02043 (18)0.01589 (17)0.01541 (17)−0.00603 (12)0.00188 (12)−0.00533 (13)
Zn20.01946 (18)0.01542 (17)0.01495 (17)−0.00544 (12)0.00213 (12)−0.00527 (12)
Cl10.0225 (4)0.0360 (4)0.0261 (4)−0.0062 (3)0.0062 (3)0.0008 (3)
Cl20.0209 (3)0.0194 (3)0.0217 (3)−0.0031 (3)0.0025 (3)−0.0055 (3)
S10.0277 (4)0.0297 (4)0.0190 (3)−0.0144 (3)0.0040 (3)−0.0100 (3)
S20.0304 (4)0.0197 (3)0.0225 (4)−0.0024 (3)−0.0034 (3)−0.0101 (3)
S30.0211 (3)0.0203 (3)0.0277 (4)−0.0065 (3)0.0029 (3)−0.0095 (3)
S40.0338 (5)0.0291 (4)0.0456 (5)−0.0114 (4)−0.0118 (4)0.0033 (4)
S50.0408 (16)0.0392 (11)0.0362 (15)0.0319 (12)−0.0108 (11)−0.0212 (10)
S5'0.045 (2)0.181 (5)0.0333 (18)−0.051 (3)−0.0006 (15)−0.032 (2)
O10.0249 (10)0.0165 (9)0.0145 (9)−0.0064 (8)0.0014 (8)−0.0054 (7)
O20.0340 (12)0.0265 (11)0.0237 (11)−0.0165 (10)−0.0001 (9)−0.0094 (9)
O30.0321 (11)0.0161 (9)0.0151 (9)−0.0054 (8)−0.0010 (8)−0.0057 (8)
O40.0525 (16)0.0249 (12)0.0344 (13)0.0034 (11)−0.0096 (11)−0.0191 (11)
O50.0316 (12)0.0311 (12)0.0325 (12)−0.0062 (10)−0.0055 (10)−0.0163 (10)
O60.0447 (15)0.0339 (14)0.0351 (14)−0.0023 (12)0.0030 (12)−0.0008 (11)
O70.065 (2)0.0502 (18)0.0486 (17)0.0013 (15)−0.0322 (16)−0.0156 (14)
N10.0181 (11)0.0153 (11)0.0187 (11)−0.0070 (9)0.0035 (9)−0.0049 (9)
N20.0209 (12)0.0184 (11)0.0191 (11)−0.0091 (9)0.0053 (9)−0.0064 (9)
N30.0222 (12)0.0231 (12)0.0204 (12)−0.0102 (10)0.0021 (10)−0.0071 (10)
N40.0210 (12)0.0171 (11)0.0191 (11)−0.0059 (9)0.0029 (9)−0.0063 (9)
N50.0255 (13)0.0189 (12)0.0217 (12)−0.0021 (10)−0.0020 (10)−0.0075 (10)
N60.0344 (15)0.0219 (13)0.0285 (14)0.0018 (11)−0.0041 (11)−0.0117 (11)
C10.0158 (12)0.0151 (12)0.0177 (13)−0.0018 (10)0.0003 (10)−0.0063 (10)
C20.0192 (13)0.0178 (13)0.0187 (13)−0.0055 (10)0.0024 (10)−0.0061 (11)
C30.0194 (13)0.0177 (13)0.0221 (14)−0.0044 (10)−0.0022 (11)−0.0063 (11)
C40.0261 (14)0.0217 (14)0.0170 (13)−0.0050 (11)−0.0010 (11)−0.0093 (11)
C50.0233 (14)0.0210 (14)0.0182 (13)−0.0040 (11)0.0014 (11)−0.0079 (11)
C60.0191 (13)0.0165 (13)0.0168 (13)−0.0032 (10)0.0009 (10)−0.0063 (10)
C70.0207 (13)0.0200 (14)0.0162 (13)−0.0048 (11)0.0044 (10)−0.0051 (11)
C80.0176 (13)0.0168 (13)0.0200 (13)−0.0034 (10)0.0014 (10)−0.0051 (10)
C90.0274 (15)0.0255 (15)0.0233 (15)−0.0128 (12)−0.0020 (12)−0.0075 (12)
C100.0241 (15)0.0269 (16)0.0312 (16)−0.0109 (12)−0.0042 (13)−0.0070 (13)
C110.0235 (14)0.0195 (13)0.0154 (13)−0.0097 (11)0.0036 (10)−0.0075 (11)
C120.0305 (15)0.0182 (14)0.0192 (14)−0.0071 (12)0.0027 (12)−0.0067 (11)
C130.0331 (16)0.0193 (14)0.0243 (15)−0.0076 (12)0.0047 (12)−0.0114 (12)
C140.0320 (16)0.0253 (15)0.0200 (14)−0.0106 (12)0.0024 (12)−0.0125 (12)
C150.0263 (15)0.0252 (15)0.0183 (13)−0.0077 (12)−0.0002 (11)−0.0088 (12)
C160.0224 (14)0.0183 (13)0.0184 (13)−0.0067 (11)0.0025 (11)−0.0080 (11)
C170.0227 (14)0.0212 (14)0.0171 (13)−0.0065 (11)0.0007 (11)−0.0063 (11)
C180.0242 (14)0.0205 (14)0.0191 (13)−0.0065 (11)0.0042 (11)−0.0072 (11)
C190.054 (2)0.0283 (17)0.0374 (19)0.0057 (16)−0.0094 (17)−0.0191 (15)
C200.042 (2)0.0292 (18)0.052 (2)−0.0032 (15)0.0022 (18)−0.0191 (17)
C210.0296 (16)0.0256 (16)0.0305 (16)−0.0119 (13)−0.0042 (13)−0.0086 (13)
C220.038 (2)0.053 (2)0.036 (2)−0.0224 (18)0.0152 (16)−0.0144 (18)
C240.053 (2)0.0283 (18)0.0347 (19)−0.0110 (16)0.0034 (17)−0.0096 (15)
C250.061 (3)0.095 (5)0.072 (4)−0.022 (3)0.019 (3)−0.015 (3)
C260.050 (2)0.040 (2)0.0345 (19)0.0049 (18)−0.0079 (17)−0.0133 (16)
C25'0.061 (3)0.095 (5)0.072 (4)−0.022 (3)0.019 (3)−0.015 (3)
C26'0.050 (2)0.040 (2)0.0345 (19)0.0049 (18)−0.0079 (17)−0.0133 (16)
Geometric parameters (Å, °) top
Zn1—O32.040 (2)C4—H40.9500
Zn1—O12.042 (2)C5—C61.408 (4)
Zn1—N42.134 (3)C5—H50.9500
Zn1—Cl12.2738 (8)C6—C71.441 (4)
Zn1—S22.4144 (8)C7—H70.9500
Zn2—O32.004 (2)C9—C101.514 (4)
Zn2—O12.041 (2)C9—H9A0.9900
Zn2—N12.106 (2)C9—H9B0.9900
Zn2—Cl22.3098 (8)C10—H10A0.9800
Zn2—S12.4330 (8)C10—H10B0.9800
S1—C81.704 (3)C10—H10C0.9800
S2—C181.709 (3)C11—C121.399 (4)
S3—O51.512 (2)C11—C161.420 (4)
S3—C211.776 (3)C12—C131.395 (4)
S3—C221.783 (4)C12—H120.9500
S4—O61.492 (3)C13—C141.397 (5)
S4—C23'1.725 (7)C14—C151.374 (4)
S4—C241.766 (4)C14—H140.9500
S4—C231.818 (8)C15—C161.415 (4)
S5—O71.556 (4)C15—H150.9500
S5—C261.755 (5)C16—C171.438 (4)
S5—C251.771 (8)C17—H170.9500
S5'—O71.463 (5)C19—C201.502 (5)
O1—C11.333 (3)C19—H19A0.9900
O2—C31.349 (3)C19—H19B0.9900
O2—H2O0.8400C20—H20A0.9800
O3—C111.333 (3)C20—H20B0.9800
O4—C131.354 (4)C20—H20C0.9800
O4—H4O0.8400C21—H21A0.9800
N1—C71.291 (4)C21—H21B0.9800
N1—N21.380 (3)C21—H21C0.9800
N2—C81.342 (4)C22—H22A0.9800
N2—H2N0.8800C22—H22B0.9800
N3—C81.335 (4)C22—H22C0.9800
N3—C91.465 (4)C23—H23A0.9800
N3—H3N0.8800C23—H23B0.9800
N4—C171.293 (4)C23—H23C0.9800
N4—N51.384 (3)C23'—H23D0.9800
N5—C181.341 (4)C23'—H23E0.9800
N5—H5N0.8800C23'—H23F0.9800
N6—C181.327 (4)C24—H24A0.9800
N6—C191.466 (4)C24—H24B0.9800
N6—H6N0.8800C24—H24C0.9800
C1—C21.396 (4)C25—H25A0.9800
C1—C61.428 (4)C25—H25B0.9800
C2—C31.390 (4)C25—H25C0.9800
C2—H20.9500C26—H26A0.9800
C3—C41.409 (4)C26—H26B0.9800
C4—C51.374 (4)C26—H26C0.9800
O3—Zn1—O175.75 (8)N3—C9—H9A109.9
O3—Zn1—N482.80 (9)C10—C9—H9A109.9
O1—Zn1—N4135.57 (9)N3—C9—H9B109.9
O3—Zn1—Cl1103.84 (7)C10—C9—H9B109.9
O1—Zn1—Cl1114.07 (6)H9A—C9—H9B108.3
N4—Zn1—Cl1108.60 (7)C9—C10—H10A109.5
O3—Zn1—S2148.58 (7)C9—C10—H10B109.5
O1—Zn1—S296.90 (6)H10A—C10—H10B109.5
N4—Zn1—S281.74 (7)C9—C10—H10C109.5
Cl1—Zn1—S2106.97 (3)H10A—C10—H10C109.5
O3—Zn2—O176.57 (8)H10B—C10—H10C109.5
O3—Zn2—N1142.48 (9)O3—C11—C12119.6 (3)
O1—Zn2—N184.26 (8)O3—C11—C16121.4 (3)
O3—Zn2—Cl2110.95 (7)C12—C11—C16119.0 (3)
O1—Zn2—Cl2108.05 (6)C13—C12—C11120.6 (3)
N1—Zn2—Cl2105.53 (7)C13—C12—H12119.7
O3—Zn2—S195.96 (6)C11—C12—H12119.7
O1—Zn2—S1145.34 (6)O4—C13—C12121.6 (3)
N1—Zn2—S181.81 (7)O4—C13—C14117.6 (3)
Cl2—Zn2—S1106.22 (3)C12—C13—C14120.9 (3)
C8—S1—Zn296.09 (10)C15—C14—C13118.8 (3)
C18—S2—Zn196.70 (10)C15—C14—H14120.6
O5—S3—C21106.24 (15)C13—C14—H14120.6
O5—S3—C22105.80 (18)C14—C15—C16122.0 (3)
C21—S3—C2297.28 (18)C14—C15—H15119.0
O6—S4—C23'117.6 (4)C16—C15—H15119.0
O6—S4—C24107.80 (18)C15—C16—C11118.6 (3)
C23'—S4—C2498.9 (3)C15—C16—C17117.3 (3)
O6—S4—C2397.2 (4)C11—C16—C17124.2 (3)
C23'—S4—C2323.5 (4)N4—C17—C16124.5 (3)
C24—S4—C2395.6 (4)N4—C17—H17117.8
O7—S5—C26104.6 (3)C16—C17—H17117.8
O7—S5—C25104.0 (3)N6—C18—N5115.7 (3)
C26—S5—C2594.9 (3)N6—C18—S2121.2 (2)
C1—O1—Zn1127.72 (17)N5—C18—S2123.1 (2)
C1—O1—Zn2129.08 (17)N6—C19—C20110.2 (3)
Zn1—O1—Zn2102.82 (9)N6—C19—H19A109.6
C3—O2—H2O109.5C20—C19—H19A109.6
C11—O3—Zn2126.62 (18)N6—C19—H19B109.6
C11—O3—Zn1128.58 (18)C20—C19—H19B109.6
Zn2—O3—Zn1104.24 (9)H19A—C19—H19B108.1
C13—O4—H4O109.5C19—C20—H20A109.5
S5'—O7—S510.9 (3)C19—C20—H20B109.5
C7—N1—N2115.9 (2)H20A—C20—H20B109.5
C7—N1—Zn2127.8 (2)C19—C20—H20C109.5
N2—N1—Zn2116.14 (17)H20A—C20—H20C109.5
C8—N2—N1121.1 (2)H20B—C20—H20C109.5
C8—N2—H2N119.4S3—C21—H21A109.5
N1—N2—H2N119.4S3—C21—H21B109.5
C8—N3—C9124.5 (3)H21A—C21—H21B109.5
C8—N3—H3N117.8S3—C21—H21C109.5
C9—N3—H3N117.8H21A—C21—H21C109.5
C17—N4—N5115.4 (3)H21B—C21—H21C109.5
C17—N4—Zn1127.1 (2)S3—C22—H22A109.5
N5—N4—Zn1116.46 (18)S3—C22—H22B109.5
C18—N5—N4120.4 (3)H22A—C22—H22B109.5
C18—N5—H5N119.8S3—C22—H22C109.5
N4—N5—H5N119.8H22A—C22—H22C109.5
C18—N6—C19124.4 (3)H22B—C22—H22C109.5
C18—N6—H6N117.8S4—C23—H23A109.5
C19—N6—H6N117.8S4—C23—H23B109.5
O1—C1—C2119.8 (2)S4—C23—H23C109.5
O1—C1—C6121.7 (2)S4—C23'—H23D109.5
C2—C1—C6118.5 (3)S4—C23'—H23E109.5
C3—C2—C1121.6 (3)H23D—C23'—H23E109.5
C3—C2—H2119.2S4—C23'—H23F109.5
C1—C2—H2119.2H23D—C23'—H23F109.5
O2—C3—C2117.4 (3)H23E—C23'—H23F109.5
O2—C3—C4122.5 (3)S4—C24—H24A109.5
C2—C3—C4120.2 (3)S4—C24—H24B109.5
C5—C4—C3118.7 (3)H24A—C24—H24B109.5
C5—C4—H4120.6S4—C24—H24C109.5
C3—C4—H4120.6H24A—C24—H24C109.5
C4—C5—C6122.4 (3)H24B—C24—H24C109.5
C4—C5—H5118.8S5—C25—H25A109.5
C6—C5—H5118.8S5—C25—H25B109.5
C5—C6—C1118.6 (3)H25A—C25—H25B109.5
C5—C6—C7117.6 (3)S5—C25—H25C109.5
C1—C6—C7123.8 (2)H25A—C25—H25C109.5
N1—C7—C6125.0 (3)H25B—C25—H25C109.5
N1—C7—H7117.5S5—C26—H26A109.5
C6—C7—H7117.5S5—C26—H26B109.5
N3—C8—N2115.8 (3)H26A—C26—H26B109.5
N3—C8—S1121.7 (2)S5—C26—H26C109.5
N2—C8—S1122.5 (2)H26A—C26—H26C109.5
N3—C9—C10109.1 (3)H26B—C26—H26C109.5
O3—Zn2—S1—C8−152.58 (12)S2—Zn1—N4—N511.49 (18)
O1—Zn2—S1—C8−77.64 (15)C17—N4—N5—C18−179.2 (3)
N1—Zn2—S1—C8−10.33 (12)Zn1—N4—N5—C18−9.7 (3)
Cl2—Zn2—S1—C893.54 (10)Zn1—O1—C1—C2−33.5 (4)
O3—Zn1—S2—C18−70.75 (16)Zn2—O1—C1—C2154.7 (2)
O1—Zn1—S2—C18−144.63 (12)Zn1—O1—C1—C6145.8 (2)
N4—Zn1—S2—C18−9.46 (12)Zn2—O1—C1—C6−26.0 (4)
Cl1—Zn1—S2—C1897.56 (11)O1—C1—C2—C3179.8 (3)
O3—Zn1—O1—C1−179.4 (2)C6—C1—C2—C30.5 (4)
N4—Zn1—O1—C1−115.8 (2)C1—C2—C3—O2−179.5 (3)
Cl1—Zn1—O1—C181.5 (2)C1—C2—C3—C4−1.1 (4)
S2—Zn1—O1—C1−30.5 (2)O2—C3—C4—C5178.8 (3)
O3—Zn1—O1—Zn2−5.97 (8)C2—C3—C4—C50.4 (4)
N4—Zn1—O1—Zn257.69 (15)C3—C4—C5—C61.0 (5)
Cl1—Zn1—O1—Zn2−104.99 (8)C4—C5—C6—C1−1.6 (4)
S2—Zn1—O1—Zn2142.92 (7)C4—C5—C6—C7−178.3 (3)
O3—Zn2—O1—C1179.4 (2)O1—C1—C6—C5−178.4 (3)
N1—Zn2—O1—C131.9 (2)C2—C1—C6—C50.9 (4)
Cl2—Zn2—O1—C1−72.6 (2)O1—C1—C6—C7−2.0 (4)
S1—Zn2—O1—C198.5 (2)C2—C1—C6—C7177.3 (3)
O3—Zn2—O1—Zn16.05 (9)N2—N1—C7—C6−177.5 (3)
N1—Zn2—O1—Zn1−141.47 (10)Zn2—N1—C7—C67.3 (4)
Cl2—Zn2—O1—Zn1114.05 (7)C5—C6—C7—N1−172.4 (3)
S1—Zn2—O1—Zn1−74.86 (13)C1—C6—C7—N111.1 (5)
O1—Zn2—O3—C11−178.1 (3)C9—N3—C8—N2−179.8 (3)
N1—Zn2—O3—C11−116.8 (2)C9—N3—C8—S1−0.2 (4)
Cl2—Zn2—O3—C1177.4 (2)N1—N2—C8—N3−177.2 (2)
S1—Zn2—O3—C11−32.5 (2)N1—N2—C8—S13.3 (4)
O1—Zn2—O3—Zn1−6.10 (9)Zn2—S1—C8—N3−172.0 (2)
N1—Zn2—O3—Zn155.23 (18)Zn2—S1—C8—N27.5 (3)
Cl2—Zn2—O3—Zn1−110.56 (8)C8—N3—C9—C10171.2 (3)
S1—Zn2—O3—Zn1139.53 (8)Zn2—O3—C11—C12−41.2 (4)
O1—Zn1—O3—C11178.0 (3)Zn1—O3—C11—C12148.7 (2)
N4—Zn1—O3—C1137.2 (2)Zn2—O3—C11—C16138.4 (2)
Cl1—Zn1—O3—C11−70.3 (2)Zn1—O3—C11—C16−31.7 (4)
S2—Zn1—O3—C1198.2 (2)O3—C11—C12—C13179.6 (3)
O1—Zn1—O3—Zn26.12 (9)C16—C11—C12—C130.0 (4)
N4—Zn1—O3—Zn2−134.67 (11)C11—C12—C13—O4177.0 (3)
Cl1—Zn1—O3—Zn2117.88 (8)C11—C12—C13—C14−3.2 (5)
S2—Zn1—O3—Zn2−73.63 (15)O4—C13—C14—C15−176.7 (3)
C26—S5—O7—S5'−86.0 (14)C12—C13—C14—C153.5 (5)
C25—S5—O7—S5'13.0 (13)C13—C14—C15—C16−0.6 (5)
O3—Zn2—N1—C7−81.3 (3)C14—C15—C16—C11−2.6 (4)
O1—Zn2—N1—C7−22.2 (3)C14—C15—C16—C17178.8 (3)
Cl2—Zn2—N1—C785.0 (3)O3—C11—C16—C15−176.8 (3)
S1—Zn2—N1—C7−170.4 (3)C12—C11—C16—C152.8 (4)
O3—Zn2—N1—N2103.6 (2)O3—C11—C16—C171.7 (4)
O1—Zn2—N1—N2162.6 (2)C12—C11—C16—C17−178.6 (3)
Cl2—Zn2—N1—N2−90.20 (19)N5—N4—C17—C16−178.0 (3)
S1—Zn2—N1—N214.45 (18)Zn1—N4—C17—C1613.8 (4)
C7—N1—N2—C8169.5 (3)C15—C16—C17—N4−175.0 (3)
Zn2—N1—N2—C8−14.7 (3)C11—C16—C17—N46.5 (5)
O3—Zn1—N4—C17−27.9 (2)C19—N6—C18—N5−172.4 (3)
O1—Zn1—N4—C17−89.0 (3)C19—N6—C18—S28.1 (5)
Cl1—Zn1—N4—C1774.4 (3)N4—N5—C18—N6179.5 (3)
S2—Zn1—N4—C17179.6 (3)N4—N5—C18—S2−1.0 (4)
O3—Zn1—N4—N5164.0 (2)Zn1—S2—C18—N6−171.6 (3)
O1—Zn1—N4—N5102.9 (2)Zn1—S2—C18—N59.0 (3)
Cl1—Zn1—N4—N5−93.72 (19)C18—N6—C19—C20170.8 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O50.841.852.623 (3)153
O4—H4O···O60.841.812.645 (4)171
N2—H2N···Cl2i0.882.433.251 (2)156
N3—H3N···Cl2i0.882.513.319 (3)153
N5—H5N···O70.881.902.706 (4)152
N6—H6N···O70.882.052.834 (4)148
Symmetry codes: (i) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O50.841.852.623 (3)153
O4—H4O···O60.841.812.645 (4)171
N2—H2N···Cl2i0.882.433.251 (2)156
N3—H3N···Cl2i0.882.513.319 (3)153
N5—H5N···O70.881.902.706 (4)152
N6—H6N···O70.882.052.834 (4)148
Symmetry codes: (i) −x+1, −y, −z+1.
Acknowledgements top

We thank the University of Malaya (grant No. PS197/2008 A) and the Ministry of Science and Technology (grant No. ESc 02–02-11-SF0033) for supporting this study. KWT thanks the Ministry of Higher Education for an SLAI scholarship.

references
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