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Acta Cryst. (2009). E65, m61-m62    [ doi:10.1107/S160053680804169X ]

(4-Hydroxy-2-oxidobenzaldehyde thiosemicarbazonato-[kappa]3O2,N1,S)(1,10-phenanthroline-[kappa]2N,N')zinc(II) dimethyl sulfoxide disolvate monohydrate

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

Abstract top

The ZnII atom in the title compound, [Zn(C8H7N3O2S)(C12H8N2)]·2C2H6OS·H2O, is N,N'-chelated by the N-heterocycle and N,O,S-chelated by the deprotonated Schiff base in a distorted square-pyramidal enviroment. Hydrogen bonds link the mononuclear molecule, the water and the dimethyl sulfoxide (DMSO) molecules into a linear chain motif. One DMSO molecule is disordered over two positions in respect of the S atom in an approximate 1:1 ratio.

Related literature top

For reports of the metal derivatives of 2,4-dihydroxybenzaldehyde thiosemicarbazone, see: Broomhead & Dwyer (1961); Gingras et al. (1960); Liu et al. (1974); Luo et al. (1988); Mayadeo et al. (1986); Onuska et al. (1996); Shen & Li (2006); Zhu et al. (1991a,b).

Experimental top

Zinc acetate monohydrate (0.22 g, 1 mmol), 2,4-dihydroxybenzaldehyde thiosemicarbazone (0.21 g, 1 mmol) and 1,10-phenanthroline (0.20 g, 1 mmol) were heated in ethanol (50 ml) to give a yellow solution. The compound that separated on cooling the solution was recrystallized from DMSO.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95– to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The amino and hydroxy H-atoms were similarly placed. The water H-atoms were placed in chemically sensible positions on the basis of hydrogen bonding but were not refined. Their temperature factors were similarly tied.

One of the two DMSO molecules is disodered in the sulfur atom only. The disorder refined to a 0.56 (1):0.44 ratio.

The middle six-membered ring of the phenanthroline unit was refined as a rigid hexagon of 1.39 Å sides. The N4 and C12 atoms of the unit were restrained to be nearly isotropic; a tight restraint was used.

The final difference Fourier map had a peak in the vicinity of N1 and a hole in the vicinity of Zn1.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 Zn(C12H8N2)(C8H7N3O2S).2DMSO.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii. The disorder in the DMSO is not shown.
(4-Hydroxy-2-oxidobenzaldehyde thiosemicarbazonato-κ3O2,N1,S)(1,10- phenanthroline-κ2N,N')zinc(II) dimethyl sulfoxide disolvate monohydrate top
Crystal data top
[Zn(C8H7N3O2S)(C12H8N2)]·2C2H6OS·H2OZ = 2
Mr = 629.07F(000) = 652
Triclinic, P1Dx = 1.563 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3582 (5) ÅCell parameters from 932 reflections
b = 9.8181 (5) Åθ = 2.2–21.9°
c = 15.2913 (8) ŵ = 1.20 mm−1
α = 73.641 (3)°T = 100 K
β = 82.482 (4)°Prism, yellow
γ = 88.059 (4)°0.05 × 0.01 × 0.01 mm
V = 1336.5 (1) Å3
Data collection top
Bruker SMART APEX
diffractometer		6125 independent reflections
Radiation source: fine-focus sealed tube3397 reflections with I > 2σ(I)
graphiteRint = 0.097
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.943, Tmax = 0.988k = −12→12
12760 measured reflectionsl = −19→19
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0989P)2]
where P = (Fo2 + 2Fc2)/3
6125 reflections(Δ/σ)max = 0.001
344 parametersΔρmax = 1.51 e Å−3
27 restraintsΔρmin = −1.29 e Å−3
Crystal data top
[Zn(C8H7N3O2S)(C12H8N2)]·2C2H6OS·H2Oγ = 88.059 (4)°
Mr = 629.07V = 1336.5 (1) Å3
Triclinic, P1Z = 2
a = 9.3582 (5) ÅMo Kα radiation
b = 9.8181 (5) ŵ = 1.20 mm−1
c = 15.2913 (8) ÅT = 100 K
α = 73.641 (3)°0.05 × 0.01 × 0.01 mm
β = 82.482 (4)°
Data collection top
Bruker SMART APEX
diffractometer		6125 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3397 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.988Rint = 0.097
12760 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.211Δρmax = 1.51 e Å−3
S = 0.98Δρmin = −1.29 e Å−3
6125 reflectionsAbsolute structure: ?
344 parametersFlack parameter: ?
27 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.78197 (8)1.15841 (8)0.72088 (5)0.0148 (2)
S10.86430 (18)1.30637 (17)0.80123 (11)0.0196 (4)
S20.30700 (19)0.28436 (18)0.79460 (12)0.0228 (4)
S31.2635 (3)1.5316 (3)0.9107 (2)0.0249 (10)0.564 (6)
S3'1.1708 (4)1.5622 (4)0.9722 (3)0.0235 (13)0.436 (6)
O10.6115 (5)1.0571 (4)0.7064 (3)0.0183 (10)
O20.4103 (5)0.6534 (5)0.6604 (3)0.0206 (10)
H20.40480.56480.68180.031*
O30.4176 (5)0.3697 (5)0.7213 (3)0.0254 (11)
O41.1918 (7)1.4255 (6)0.9740 (4)0.067 (2)
O1W0.5152 (5)0.8171 (5)0.4620 (4)0.0352 (13)
H1W10.45960.84550.42170.053*
H1W20.46640.77450.51180.053*
N10.8024 (6)1.0029 (6)0.8431 (4)0.0180 (12)
N20.8839 (6)1.0295 (6)0.9059 (4)0.0173 (12)
N30.9991 (6)1.1973 (6)0.9465 (4)0.0198 (12)
H311.02751.12970.99220.024*
H321.02431.28600.93850.024*
N40.7906 (6)1.3147 (6)0.5889 (4)0.0169 (12)
N50.9576 (5)1.0814 (5)0.6433 (4)0.0141 (11)
C10.6018 (7)0.9163 (7)0.7315 (4)0.0166 (14)
C20.5111 (6)0.8529 (6)0.6879 (4)0.0147 (13)
H2A0.45590.91170.64390.018*
C30.4999 (7)0.7065 (7)0.7073 (4)0.0177 (14)
C40.5791 (7)0.6167 (7)0.7718 (4)0.0182 (14)
H40.57470.51650.78340.022*
C50.6633 (7)0.6775 (7)0.8177 (4)0.0174 (14)
H50.71620.61710.86240.021*
C60.6750 (7)0.8259 (6)0.8015 (4)0.0144 (13)
C70.7622 (6)0.8737 (7)0.8587 (4)0.0152 (13)
H70.79150.80550.91080.018*
C80.9168 (7)1.1651 (7)0.8889 (4)0.0163 (14)
C90.7054 (7)1.4278 (6)0.5623 (5)0.0173 (14)
H90.62591.44270.60400.021*
C100.7303 (7)1.5230 (7)0.4761 (4)0.0180 (14)
H100.66721.60120.45890.022*
C110.8459 (7)1.5049 (7)0.4152 (5)0.0194 (14)
H110.86371.57120.35630.023*
C120.9394 (4)1.3858 (3)0.4409 (3)0.0162 (13)
C141.0583 (4)1.3616 (4)0.3825 (2)0.0191 (14)
H141.08021.42550.32300.023*
C151.1451 (4)1.2440 (4)0.4113 (2)0.0189 (14)
H151.22641.22740.37140.023*
C161.1131 (4)1.1505 (3)0.4984 (3)0.0180 (14)
C170.9942 (4)1.1746 (4)0.5568 (2)0.0143 (13)
C130.9074 (4)1.2923 (4)0.5280 (2)0.0147 (13)
C181.1962 (7)1.0255 (7)0.5292 (5)0.0184 (14)
H181.27841.00620.49110.022*
C191.1562 (6)0.9336 (7)0.6142 (4)0.0164 (14)
H191.20950.84930.63530.020*
C201.0360 (7)0.9656 (6)0.6694 (5)0.0167 (14)
H201.00930.90130.72830.020*
C210.2630 (8)0.1380 (7)0.7548 (5)0.0269 (16)
H21A0.22230.17370.69670.040*
H21B0.19220.07680.80070.040*
H21C0.35030.08340.74520.040*
C220.4045 (8)0.1879 (8)0.8850 (5)0.0302 (17)
H22A0.48030.13220.86070.045*
H22B0.33870.12400.93300.045*
H22C0.44830.25450.91100.045*
C231.3333 (8)1.6563 (9)0.9636 (6)0.040 (2)
H23A1.27901.64601.02450.060*0.564 (6)
H23B1.32311.75350.92490.060*0.564 (6)
H23C1.43541.63640.96990.060*0.564 (6)
H23D1.40921.61880.92860.060*0.436 (6)
H23E1.35841.64581.02410.060*0.436 (6)
H23F1.32021.75510.93370.060*0.436 (6)
C241.1292 (9)1.6561 (9)0.8566 (6)0.053 (3)
H24A1.05681.60400.83790.080*0.564 (6)
H24B1.17681.72620.80250.080*0.564 (6)
H24C1.08231.70470.90050.080*0.564 (6)
H24D1.07791.59410.83300.080*0.436 (6)
H24E1.21741.68650.81690.080*0.436 (6)
H24F1.07091.73750.85950.080*0.436 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0175 (4)0.0132 (4)0.0153 (4)−0.0021 (3)−0.0029 (3)−0.0061 (3)
S10.0279 (9)0.0143 (8)0.0187 (9)−0.0024 (7)−0.0078 (7)−0.0056 (7)
S20.0245 (9)0.0196 (9)0.0275 (10)−0.0028 (7)−0.0038 (8)−0.0111 (7)
S30.0274 (18)0.0231 (18)0.0235 (18)−0.0044 (13)0.0022 (14)−0.0072 (14)
S3'0.027 (2)0.022 (2)0.024 (2)−0.0031 (16)−0.0019 (17)−0.0097 (17)
O10.019 (2)0.009 (2)0.028 (3)−0.0014 (18)−0.007 (2)−0.0063 (19)
O20.023 (2)0.015 (2)0.027 (3)−0.005 (2)−0.006 (2)−0.009 (2)
O30.030 (3)0.025 (3)0.027 (3)−0.008 (2)−0.004 (2)−0.016 (2)
O40.110 (6)0.026 (3)0.072 (5)−0.001 (4)−0.061 (5)−0.003 (3)
O1W0.036 (3)0.038 (3)0.033 (3)−0.009 (3)−0.012 (2)−0.008 (3)
N10.019 (3)0.019 (3)0.019 (3)−0.003 (2)−0.005 (2)−0.008 (2)
N20.021 (3)0.018 (3)0.018 (3)−0.002 (2)−0.007 (2)−0.012 (2)
N30.031 (3)0.012 (3)0.021 (3)−0.002 (2)−0.015 (3)−0.007 (2)
N40.019 (2)0.018 (2)0.020 (3)−0.004 (2)−0.005 (2)−0.013 (2)
N50.016 (3)0.012 (3)0.017 (3)0.000 (2)−0.009 (2)−0.005 (2)
C10.015 (3)0.018 (3)0.020 (3)−0.002 (3)−0.006 (3)−0.008 (3)
C20.011 (3)0.016 (3)0.019 (3)−0.002 (2)−0.002 (3)−0.008 (3)
C30.018 (3)0.017 (3)0.019 (3)−0.002 (3)0.002 (3)−0.009 (3)
C40.021 (3)0.011 (3)0.022 (4)−0.007 (3)0.005 (3)−0.006 (3)
C50.017 (3)0.015 (3)0.019 (3)−0.007 (3)0.002 (3)−0.004 (3)
C60.017 (3)0.011 (3)0.016 (3)−0.002 (2)0.003 (3)−0.008 (3)
C70.016 (3)0.015 (3)0.012 (3)−0.006 (3)0.000 (3)−0.001 (3)
C80.016 (3)0.020 (3)0.015 (3)−0.005 (3)0.001 (3)−0.009 (3)
C90.018 (3)0.015 (3)0.023 (4)0.004 (3)−0.007 (3)−0.009 (3)
C100.021 (3)0.014 (3)0.024 (4)0.001 (3)−0.007 (3)−0.010 (3)
C110.022 (3)0.013 (3)0.021 (4)−0.001 (3)−0.004 (3)−0.002 (3)
C120.019 (3)0.015 (3)0.019 (3)−0.005 (2)−0.007 (2)−0.010 (2)
C140.024 (3)0.015 (3)0.020 (3)−0.005 (3)−0.002 (3)−0.007 (3)
C150.016 (3)0.020 (3)0.025 (4)−0.005 (3)0.000 (3)−0.014 (3)
C160.015 (3)0.019 (3)0.024 (4)−0.006 (3)−0.002 (3)−0.012 (3)
C170.014 (3)0.013 (3)0.018 (3)−0.007 (2)−0.001 (3)−0.009 (3)
C130.018 (3)0.013 (3)0.018 (3)−0.003 (3)−0.005 (3)−0.011 (3)
C180.014 (3)0.021 (3)0.026 (4)0.002 (3)−0.008 (3)−0.015 (3)
C190.013 (3)0.016 (3)0.023 (4)0.003 (3)−0.008 (3)−0.009 (3)
C200.018 (3)0.011 (3)0.023 (3)0.004 (3)−0.005 (3)−0.008 (3)
C210.029 (4)0.020 (4)0.035 (4)−0.002 (3)−0.004 (3)−0.012 (3)
C220.038 (4)0.026 (4)0.026 (4)−0.001 (3)−0.009 (3)−0.004 (3)
C230.043 (5)0.037 (5)0.042 (5)−0.014 (4)0.001 (4)−0.014 (4)
C240.058 (6)0.042 (5)0.049 (6)0.004 (5)−0.026 (5)0.012 (5)
Geometric parameters (Å, °) top
Zn1—O11.976 (4)C6—C71.448 (9)
Zn1—N12.081 (5)C7—H70.9500
Zn1—N52.143 (5)C9—C101.381 (9)
Zn1—N42.157 (5)C9—H90.9500
Zn1—S12.3542 (18)C10—C111.373 (9)
S1—C81.744 (7)C10—H100.9500
S2—O31.502 (5)C11—C121.432 (7)
S2—C221.782 (7)C11—H110.9500
S2—C211.790 (7)C12—C141.3900
S3—O41.335 (7)C12—C131.3900
S3—C231.825 (8)C14—C151.3900
S3—C241.832 (8)C14—H140.9500
S3—H23D1.7249C15—C161.3900
S3'—O41.342 (7)C15—H150.9500
S3'—C231.777 (8)C16—C171.3900
S3'—C241.834 (9)C16—C181.427 (7)
O1—C11.329 (7)C17—C131.3900
O2—C31.373 (8)C18—C191.371 (9)
O2—H20.8400C18—H180.9500
O1W—H1W10.8400C19—C201.397 (9)
O1W—H1W20.8400C19—H190.9500
N1—C71.282 (8)C20—H200.9500
N1—N21.385 (7)C21—H21A0.9800
N2—C81.321 (8)C21—H21B0.9800
N3—C81.349 (8)C21—H21C0.9800
N3—H310.8800C22—H22A0.9800
N3—H320.8800C22—H22B0.9800
N4—C91.344 (8)C22—H22C0.9800
N4—C131.394 (6)C23—H23A0.9800
N5—C201.325 (8)C23—H23B0.9800
N5—C171.388 (6)C23—H23C0.9800
C1—C21.405 (8)C23—H23D0.9601
C1—C61.421 (9)C23—H23E0.9600
C2—C31.389 (9)C23—H23F0.9600
C2—H2A0.9500C24—H24A0.9800
C3—C41.398 (9)C24—H24B0.9800
C4—C51.373 (9)C24—H24C0.9800
C4—H40.9500C24—H24D0.9599
C5—C61.413 (8)C24—H24E0.9600
C5—H50.9500C24—H24F0.9601
O1—Zn1—N189.26 (19)C14—C12—C13120.0
O1—Zn1—N5104.25 (19)C14—C12—C11122.6 (4)
N1—Zn1—N594.6 (2)C13—C12—C11117.4 (4)
O1—Zn1—N495.47 (18)C12—C14—C15120.0
N1—Zn1—N4172.4 (2)C12—C14—H14120.0
N5—Zn1—N478.52 (19)C15—C14—H14120.0
O1—Zn1—S1143.98 (15)C14—C15—C16120.0
N1—Zn1—S182.37 (15)C14—C15—H15120.0
N5—Zn1—S1111.28 (14)C16—C15—H15120.0
N4—Zn1—S197.11 (14)C17—C16—C15120.0
C8—S1—Zn193.9 (2)C17—C16—C18118.2 (4)
O3—S2—C22105.7 (3)C15—C16—C18121.7 (4)
O3—S2—C21105.6 (3)N5—C17—C13118.7 (3)
C22—S2—C2197.8 (4)N5—C17—C16121.3 (3)
O4—S3—C23111.0 (4)C13—C17—C16120.0
O4—S3—C24107.3 (4)C17—C13—C12120.0
C23—S3—C2493.9 (4)C17—C13—N4118.5 (3)
O4—S3—H23D124.6C12—C13—N4121.5 (3)
C24—S3—H23D111.8C19—C18—C16119.4 (6)
O4—S3'—C23113.4 (5)C19—C18—H18120.3
O4—S3'—C24106.8 (4)C16—C18—H18120.3
C23—S3'—C2495.5 (4)C18—C19—C20119.2 (6)
C1—O1—Zn1122.6 (4)C18—C19—H19120.4
C3—O2—H2109.5C20—C19—H19120.4
S3—O4—S3'57.4 (3)N5—C20—C19122.9 (6)
H1W1—O1W—H1W2108.8N5—C20—H20118.5
C7—N1—N2115.8 (5)C19—C20—H20118.5
C7—N1—Zn1123.3 (4)S2—C21—H21A109.5
N2—N1—Zn1119.9 (4)S2—C21—H21B109.5
C8—N2—N1113.3 (5)H21A—C21—H21B109.5
C8—N3—H31120.0S2—C21—H21C109.5
C8—N3—H32120.0H21A—C21—H21C109.5
H31—N3—H32120.0H21B—C21—H21C109.5
C9—N4—C13119.3 (5)S2—C22—H22A109.5
C9—N4—Zn1128.9 (4)S2—C22—H22B109.5
C13—N4—Zn1111.7 (3)H22A—C22—H22B109.5
C20—N5—C17119.0 (5)S2—C22—H22C109.5
C20—N5—Zn1128.8 (4)H22A—C22—H22C109.5
C17—N5—Zn1112.1 (3)H22B—C22—H22C109.5
O1—C1—C2118.1 (6)S3—C23—H23A109.5
O1—C1—C6124.0 (6)S3'—C23—H23B108.6
C2—C1—C6117.8 (6)S3—C23—H23B109.5
C3—C2—C1121.6 (6)H23A—C23—H23B109.5
C3—C2—H2A119.2S3'—C23—H23C139.0
C1—C2—H2A119.2S3—C23—H23C109.5
O2—C3—C2117.8 (6)H23A—C23—H23C109.5
O2—C3—C4121.4 (6)H23B—C23—H23C109.5
C2—C3—C4120.8 (6)S3'—C23—H23D109.5
C5—C4—C3118.0 (6)S3'—C23—H23E109.4
C5—C4—H4121.0S3—C23—H23E132.4
C3—C4—H4121.0H23D—C23—H23E109.5
C4—C5—C6123.0 (6)S3'—C23—H23F109.6
C4—C5—H5118.5S3—C23—H23F115.8
C6—C5—H5118.5H23D—C23—H23F109.5
C5—C6—C1118.5 (6)H23E—C23—H23F109.5
C5—C6—C7116.5 (6)S3—C24—H24A109.5
C1—C6—C7125.0 (6)S3'—C24—H24A110.7
N1—C7—C6123.8 (6)S3—C24—H24B109.5
N1—C7—H7118.1S3'—C24—H24B136.8
C6—C7—H7118.1H24A—C24—H24B109.5
N2—C8—N3116.1 (6)S3—C24—H24C109.5
N2—C8—S1127.2 (5)H24A—C24—H24C109.5
N3—C8—S1116.7 (5)H24B—C24—H24C109.5
N4—C9—C10121.8 (6)S3—C24—H24D99.6
N4—C9—H9119.1S3'—C24—H24D109.8
C10—C9—H9119.1S3—C24—H24E76.3
C11—C10—C9120.1 (6)S3'—C24—H24E109.4
C11—C10—H10119.9H24D—C24—H24E109.5
C9—C10—H10119.9S3—C24—H24F145.6
C10—C11—C12119.8 (6)S3'—C24—H24F109.3
C10—C11—H11120.1H24D—C24—H24F109.5
C12—C11—H11120.1H24E—C24—H24F109.5
O1—Zn1—S1—C891.0 (3)C1—C6—C7—N1−11.7 (10)
N1—Zn1—S1—C812.9 (3)N1—N2—C8—N3−178.5 (5)
N5—Zn1—S1—C8−79.0 (3)N1—N2—C8—S12.1 (8)
N4—Zn1—S1—C8−159.5 (3)Zn1—S1—C8—N2−13.0 (6)
N1—Zn1—O1—C1−36.1 (5)Zn1—S1—C8—N3167.7 (5)
N5—Zn1—O1—C158.4 (5)C13—N4—C9—C10−0.1 (9)
N4—Zn1—O1—C1137.9 (5)Zn1—N4—C9—C10176.3 (4)
S1—Zn1—O1—C1−112.0 (5)N4—C9—C10—C11−1.0 (10)
C23—S3—O4—S3'47.1 (4)C9—C10—C11—C120.9 (9)
C24—S3—O4—S3'−54.3 (4)C10—C11—C12—C14−179.9 (5)
C23—S3'—O4—S3−49.9 (4)C10—C11—C12—C130.2 (7)
C24—S3'—O4—S354.0 (4)C13—C12—C14—C150.0
O1—Zn1—N1—C729.5 (5)C11—C12—C14—C15−179.9 (5)
N5—Zn1—N1—C7−74.8 (5)C12—C14—C15—C160.0
S1—Zn1—N1—C7174.3 (5)C14—C15—C16—C170.0
O1—Zn1—N1—N2−161.9 (5)C14—C15—C16—C18177.5 (5)
N5—Zn1—N1—N293.9 (5)C20—N5—C17—C13176.9 (4)
S1—Zn1—N1—N2−17.0 (4)Zn1—N5—C17—C13−7.0 (4)
C7—N1—N2—C8−177.1 (6)C20—N5—C17—C16−1.7 (6)
Zn1—N1—N2—C813.4 (7)Zn1—N5—C17—C16174.5 (2)
O1—Zn1—N4—C974.9 (5)C15—C16—C17—N5178.5 (4)
N5—Zn1—N4—C9178.4 (5)C18—C16—C17—N50.9 (5)
S1—Zn1—N4—C9−71.3 (5)C15—C16—C17—C130.0
O1—Zn1—N4—C13−108.5 (4)C18—C16—C17—C13−177.6 (4)
N5—Zn1—N4—C13−5.0 (3)N5—C17—C13—C12−178.5 (4)
S1—Zn1—N4—C13105.3 (3)C16—C17—C13—C120.0
O1—Zn1—N5—C20−85.1 (5)N5—C17—C13—N42.6 (5)
N1—Zn1—N5—C205.2 (5)C16—C17—C13—N4−178.8 (4)
N4—Zn1—N5—C20−177.9 (6)C14—C12—C13—C170.0
S1—Zn1—N5—C2088.8 (5)C11—C12—C13—C17179.9 (4)
N1—Zn1—N5—C17−170.5 (3)C14—C12—C13—N4178.8 (4)
N4—Zn1—N5—C176.3 (3)C11—C12—C13—N4−1.3 (5)
S1—Zn1—N5—C17−86.9 (3)C9—N4—C13—C17−180.0 (4)
Zn1—O1—C1—C2−154.9 (4)Zn1—N4—C13—C173.1 (4)
Zn1—O1—C1—C626.7 (8)C9—N4—C13—C121.2 (7)
O1—C1—C2—C3177.1 (6)Zn1—N4—C13—C12−175.7 (2)
C6—C1—C2—C3−4.4 (9)C17—C16—C18—C190.4 (7)
C1—C2—C3—O2−179.0 (6)C15—C16—C18—C19−177.2 (4)
C1—C2—C3—C40.2 (10)C16—C18—C19—C20−0.9 (9)
O2—C3—C4—C5−178.2 (6)C17—N5—C20—C191.1 (9)
C2—C3—C4—C52.6 (9)Zn1—N5—C20—C19−174.3 (5)
C3—C4—C5—C6−1.1 (10)C18—C19—C20—N50.2 (10)
C4—C5—C6—C1−3.1 (9)O4—S3'—C23—S345.0 (4)
C4—C5—C6—C7176.9 (6)C24—S3'—C23—S3−66.0 (3)
O1—C1—C6—C5−175.9 (6)O4—S3—C23—S3'−44.3 (4)
C2—C1—C6—C55.7 (9)C24—S3—C23—S3'65.9 (3)
O1—C1—C6—C74.1 (10)O4—S3—C24—S3'49.6 (4)
C2—C1—C6—C7−174.4 (6)C23—S3—C24—S3'−63.8 (3)
N2—N1—C7—C6179.2 (5)O4—S3'—C24—S3−49.1 (4)
Zn1—N1—C7—C6−11.8 (9)C23—S3'—C24—S367.4 (3)
C5—C6—C7—N1168.3 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.841.842.679 (6)172
N3—H31···N2i0.882.112.984 (8)174
N3—H32···O40.882.333.074 (8)143
O1w—H1w1···O1ii0.842.112.911 (7)160
O1w—H1w2···O20.842.253.055 (7)161
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.841.842.679 (6)172
N3—H31···N2i0.882.112.984 (8)174
N3—H32···O40.882.333.074 (8)143
O1w—H1w1···O1ii0.842.112.911 (7)160
O1w—H1w2···O20.842.253.055 (7)161
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+2, −z+1.
Acknowledgements top

We thank the University of Malaya (PJP FS316/2008 C) for supporting this study; KWT thanks the Ministry of Higher Education for an SLAI scholarship.

references
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