metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages m61-m62

(4-Hydr­­oxy-2-oxidobenzaldehyde thio­semicarbazonato-κ3O2,N1,S)(1,10-phenanthroline-κ2N,N′)zinc(II) di­methyl sulfoxide disolvate monohydrate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, bFaculty of Engineering and Science, Universiti Tunku Abdul Rahman, 53300 Kuala Lumpur, Malaysia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: mjamil@um.edu.my

(Received 3 December 2008; accepted 9 December 2008; online 13 December 2008)

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

For reports of the metal derivatives of 2,4-dihydroxy­benzaldehyde thio­semicarbazone, see: Broomhead & Dwyer (1961[Broomhead, J. A. & Dwyer, F. P. (1961). Aust. J. Chem. 14, 250]); Gingras et al. (1960[Gingras, I. B. A., Hornal, R. W. & Bayley, C. H. (1960). Can. J. Chem. 38, 712-719.]); Liu et al. (1974[Liu, H.-C., Chen, S.-T., Sun, P.-J., Chin, Y.-Y. & Yang, C.-H. (1974). Huaxue, pp. 38-48.]); Luo et al. (1988[Luo, Z.-F., Yan, Z.-H., Wu, Z.-S. & Guo, W.-G. (1988). Huazhong Shifan Daxue Xuebao, Ziran Kexueban, 22, 56-60.]); Mayadeo et al. (1986[Mayadeo, M. S., Sinha, C. H. & Kale, S. S. (1986). J. Ind. Chem. Soc. 63, 694-696.]); Onuska et al. (1996[Onuska, K. D., Lahitova, N. & Carsky, J. (1996). Toxicol. Environ. Chem. 57, 163-170.]); Shen & Li (2006[Shen, Y.-M. & Li, Z.-Q. (2006). Hecheng Huaxue, 14, 126-130.]); Zhu et al. (1991a[Zhu, X.-D., Luo, Z.-F., Wu, Z. S. & Yan, Z.-H. (1991a). Zh. Neorg. Khim. 36, 1240-1243.],b[Zhu, X.-D., Luo, Z.-F., Wu, Z. S., Yan, Z.-H. & Wang, C.-G. (1991b). Gaodeng Xuexiao Huaxue Xuebao, 12, 1066-1068.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C8H7N3O2S)(C12H8N2)]·2C2H6OS·H2O

  • Mr = 629.07

  • Triclinic, [P \overline 1]

  • a = 9.3582 (5) Å

  • b = 9.8181 (5) Å

  • c = 15.2913 (8) Å

  • α = 73.641 (3)°

  • β = 82.482 (4)°

  • γ = 88.059 (4)°

  • V = 1336.5 (1) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.20 mm−1

  • T = 100 (2) K

  • 0.05 × 0.01 × 0.01 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.943, Tmax = 0.988

  • 12760 measured reflections

  • 6125 independent reflections

  • 3397 reflections with I > 2σ(I)

  • Rint = 0.097

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.211

  • S = 0.98

  • 6125 reflections

  • 344 parameters

  • 27 restraints

  • H-atom parameters constrained

  • Δρmax = 1.51 e Å−3

  • Δρmin = −1.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O3 0.84 1.84 2.679 (6) 172
N3—H31⋯N2i 0.88 2.11 2.984 (8) 174
N3—H32⋯O4 0.88 2.33 3.074 (8) 143
O1w—H1w1⋯O1ii 0.84 2.11 2.911 (7) 160
O1w—H1w2⋯O2 0.84 2.25 3.055 (7) 161
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 m3
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 mm1
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)
Graphite monochromatorRint = 0.097
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.943, Tmax = 0.988k = 1212
12760 measured reflectionsl = 1919
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 Å3
27 restraintsΔρmin = 1.29 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07427 restraints
wR(F2) = 0.211H-atom parameters constrained
S = 0.98Δρmax = 1.51 e Å3
6125 reflectionsΔρmin = 1.29 e Å3
344 parameters
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, º) 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—N111.7 (10)
N1—Zn1—S1—C812.9 (3)N1—N2—C8—N3178.5 (5)
N5—Zn1—S1—C879.0 (3)N1—N2—C8—S12.1 (8)
N4—Zn1—S1—C8159.5 (3)Zn1—S1—C8—N213.0 (6)
N1—Zn1—O1—C136.1 (5)Zn1—S1—C8—N3167.7 (5)
N5—Zn1—O1—C158.4 (5)C13—N4—C9—C100.1 (9)
N4—Zn1—O1—C1137.9 (5)Zn1—N4—C9—C10176.3 (4)
S1—Zn1—O1—C1112.0 (5)N4—C9—C10—C111.0 (10)
C23—S3—O4—S3'47.1 (4)C9—C10—C11—C120.9 (9)
C24—S3—O4—S3'54.3 (4)C10—C11—C12—C14179.9 (5)
C23—S3'—O4—S349.9 (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—C15179.9 (5)
N5—Zn1—N1—C774.8 (5)C12—C14—C15—C160.0
S1—Zn1—N1—C7174.3 (5)C14—C15—C16—C170.0
O1—Zn1—N1—N2161.9 (5)C14—C15—C16—C18177.5 (5)
N5—Zn1—N1—N293.9 (5)C20—N5—C17—C13176.9 (4)
S1—Zn1—N1—N217.0 (4)Zn1—N5—C17—C137.0 (4)
C7—N1—N2—C8177.1 (6)C20—N5—C17—C161.7 (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—C971.3 (5)C15—C16—C17—C130.0
O1—Zn1—N4—C13108.5 (4)C18—C16—C17—C13177.6 (4)
N5—Zn1—N4—C135.0 (3)N5—C17—C13—C12178.5 (4)
S1—Zn1—N4—C13105.3 (3)C16—C17—C13—C120.0
O1—Zn1—N5—C2085.1 (5)N5—C17—C13—N42.6 (5)
N1—Zn1—N5—C205.2 (5)C16—C17—C13—N4178.8 (4)
N4—Zn1—N5—C20177.9 (6)C14—C12—C13—C170.0
S1—Zn1—N5—C2088.8 (5)C11—C12—C13—C17179.9 (4)
N1—Zn1—N5—C17170.5 (3)C14—C12—C13—N4178.8 (4)
N4—Zn1—N5—C176.3 (3)C11—C12—C13—N41.3 (5)
S1—Zn1—N5—C1786.9 (3)C9—N4—C13—C17180.0 (4)
Zn1—O1—C1—C2154.9 (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—C12175.7 (2)
C6—C1—C2—C34.4 (9)C17—C16—C18—C190.4 (7)
C1—C2—C3—O2179.0 (6)C15—C16—C18—C19177.2 (4)
C1—C2—C3—C40.2 (10)C16—C18—C19—C200.9 (9)
O2—C3—C4—C5178.2 (6)C17—N5—C20—C191.1 (9)
C2—C3—C4—C52.6 (9)Zn1—N5—C20—C19174.3 (5)
C3—C4—C5—C61.1 (10)C18—C19—C20—N50.2 (10)
C4—C5—C6—C13.1 (9)O4—S3'—C23—S345.0 (4)
C4—C5—C6—C7176.9 (6)C24—S3'—C23—S366.0 (3)
O1—C1—C6—C5175.9 (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—C7174.4 (6)C23—S3—C24—S3'63.8 (3)
N2—N1—C7—C6179.2 (5)O4—S3'—C24—S349.1 (4)
Zn1—N1—C7—C611.8 (9)C23—S3'—C24—S367.4 (3)
C5—C6—C7—N1168.3 (6)
Hydrogen-bond geometry (Å, º) 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.

Experimental details

Crystal data
Chemical formula[Zn(C8H7N3O2S)(C12H8N2)]·2C2H6OS·H2O
Mr629.07
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.3582 (5), 9.8181 (5), 15.2913 (8)
α, β, γ (°)73.641 (3), 82.482 (4), 88.059 (4)
V3)1336.5 (1)
Z2
Radiation typeMo Kα
µ (mm1)1.20
Crystal size (mm)0.05 × 0.01 × 0.01
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.943, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
12760, 6125, 3397
Rint0.097
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.211, 0.98
No. of reflections6125
No. of parameters344
No. of restraints27
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.51, 1.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) 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

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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBroomhead, J. A. & Dwyer, F. P. (1961). Aust. J. Chem. 14, 250  CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGingras, I. B. A., Hornal, R. W. & Bayley, C. H. (1960). Can. J. Chem. 38, 712–719.  CrossRef CAS Web of Science Google Scholar
First citationLiu, H.-C., Chen, S.-T., Sun, P.-J., Chin, Y.-Y. & Yang, C.-H. (1974). Huaxue, pp. 38–48.  Google Scholar
First citationLuo, Z.-F., Yan, Z.-H., Wu, Z.-S. & Guo, W.-G. (1988). Huazhong Shifan Daxue Xuebao, Ziran Kexueban, 22, 56–60.  Google Scholar
First citationMayadeo, M. S., Sinha, C. H. & Kale, S. S. (1986). J. Ind. Chem. Soc. 63, 694–696.  CAS Google Scholar
First citationOnuska, K. D., Lahitova, N. & Carsky, J. (1996). Toxicol. Environ. Chem. 57, 163–170.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShen, Y.-M. & Li, Z.-Q. (2006). Hecheng Huaxue, 14, 126–130.  CAS Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar
First citationZhu, X.-D., Luo, Z.-F., Wu, Z. S. & Yan, Z.-H. (1991a). Zh. Neorg. Khim. 36, 1240–1243.  Google Scholar
First citationZhu, X.-D., Luo, Z.-F., Wu, Z. S., Yan, Z.-H. & Wang, C.-G. (1991b). Gaodeng Xuexiao Huaxue Xuebao, 12, 1066–1068.  CAS Google Scholar

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Volume 65| Part 1| January 2009| Pages m61-m62
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