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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page m1457
https://doi.org/10.1107/S1600536811038918

Tetra­aqua­bis­­(2-{[5-(pyridin-4-yl)-1,3,4-oxa­diazol-2-yl]sulfan­yl}acetato)­iron(II)

Hai-Rong Wanga* and Guo-Ting Lia

aDepartment of Environmental and Municipal Engineering, North China University of Water Conservancy and Electric Power, Zhengzhou, 450011, People's Republic of China
*Correspondence e-mail: wanghairong@ncwu.edu.cn

(Received 18 July 2011; accepted 22 September 2011; online 30 September 2011)

In the title compound, [Fe(C9H6N3O3S)2(H2O)4] or [Fe(POA)2(H2O)4], the FeII atom is located on an inversion center and is ligated by four O atoms of coordinated water mol­ecules in the equatorial plane while two POA ligands acting as monodentate ligands occupy the axial positions through their pyridyl N atoms, completing a slightly distorted octa­hedral coordination geometry. A three-dimensional supra­molecular network is formed by multiple O—H⋯O hydrogen-bonding inter­actions between the coordinated water donors and the uncoordinated carboxyl acceptors.

Related literature

For the synthesis of 5-(4-pyrid­yl)-1,3,4-oxadiazole-2-thione, see: Young & Wood (1955[Young, R. W. & Wood, K. H. (1955). J. Am. Chem. Soc. 77, 400-403.]). For metal-assisted transformation of N-benzoyl­dithio­carbazate to 5-phenyl-1,3,4-oxadiazole-2-thiol (pot) in the presence of ethyl­enediamine, and its first-row transition-metal complexes, see: Tripathi et al. (2007[Tripathi, P., Pal, A., Jancik, V., Pandey, A. K., Singh, J. & Singh, N. K. (2007). Polyhedron, 26, 2597-2602.]). For ZnII and CdII metal-organic polymers with the versatile building block 5-(4-pyrid­yl)-1,3,4-oxadiazole-2-thiol, see: Du et al. (2006[Du, M., Zhang, Z. H., Zhao, X.-J. & Xu, Q. (2006). Inorg. Chem. 45, 5785-5792.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe(C9H6N3O3S)2(H2O)4]

  • Mr = 600.37

  • Monoclinic, P 21 /c

  • a = 14.365 (3) Å

  • b = 10.709 (2) Å

  • c = 7.5709 (15) Å

  • β = 91.45 (3)°

  • V = 1164.2 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.90 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm
Data collection

  • Siemens SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.949, Tmax = 1.000

  • 12366 measured reflections

  • 2285 independent reflections

  • 2179 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.078

  • S = 1.13

  • 2285 reflections

  • 185 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Selected bond lengths (Å)

Fe1—O1 2.0605 (17)
Fe1—O2 2.1340 (18)
Fe1—N1 2.2359 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯O5i 0.83 (3) 1.87 (3) 2.691 (3) 170 (3)
O1—H1B⋯O5ii 0.83 (3) 1.82 (4) 2.649 (2) 174 (3)
O2—H2A⋯O4ii 0.82 (3) 2.07 (3) 2.896 (3) 177 (3)
O2—H2B⋯O4iii 0.84 (4) 1.98 (4) 2.817 (3) 175 (3)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1994[Siemens (1994). SAINT. Siemens Analytical X-ray Instruments 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038918/si2366sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038918/si2366Isup2.hkl

checkCIF report


Comment top

Recently, pyridyl-containing 1,3,4-oxadiazole-2-thione have been systematically explored as promising bridging ligands in coordination chemistry. Metal- assisted transformation of N-benzoyldithiocarbazate to 5-phenyl-1,3,4-oxadiazole-2-thiol (pot) in the presence of ethylenediamine, and its first row transition metal complexes were discussed by N. K. Singh and coworkers [Tripathi et al., (2007)]. A report describing ZnII and CdII metal-organic polymers with a versatile building block 5-(4-pyridyl) -1,3,4-oxadiazole-2-thiol was presented by Du et al., (2006). We purposedly engrafted the carboxylic group into the 5-(pyridin-4-yl)-1,3,4-oxadiazol-2-ylthio backbone and synthesized the multifunctional ligands 2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-ylthio)acetic acid (HPOA). Herein we report that the reaction of FeSO4.7H2O and sodium(I) salt of HPOA leads to a new complex [Fe(POA)2(H2O)4] (Fig.1).

The title compound is a mononuclear complex in which every FeII ion located at the inversion center i reproduces the whole molecule through the asymmetry unit consisting of one-half FeII, one deprotonated POA and two water molecules. In (1) the iron(II) center is ligated by four O from water molecules in the equatorial plane, and two POA anions acting as monodentate ligands and occupy the axial positions through their pyridyl nitrogen atoms coordinating to FeII, which is in an axial-elongated octahedral coordination sphere with the bond distances of Fe—O and Fe—N ranging from 2.0605 (17) to 2.2359 (18) Å (Table 1).

In (1) the uncoordinated carboxyl groups as typical hydrogen-bonding acceptors are authentically interesting in the construction of an intricate three-dimensional supramolecular network. Clearly, further aggregation of the monomers (1) is directed by the multiple hydrogen-bonding between the coordinated water donors and the uncoordinated carboxyl acceptors. Fig. 2 shows the complicated hydrogen-bonding system among monomers (1): each coordination water molecule in one monomer forms two O—H···O hydrogen bonds (Table 2) with carboxyl groups to bridge two monomers, while every carboxyl group of POA in the monomer acts as a three-connected hydrogen-bonding acceptor and adopts two different hydrogen-bonding models (bridging and chelating modes) to links with three monomers. Consequently, every monomer acts as a novel six-connected supramolecular synthon to connect with six adjacent monomers. In this way monomers (1) are arrayed to create a three-dimensional supramolecular architecture as shown in Fig. 3.

Related literature top

For the synthesis of 5-(4-pyridyl)-1,3,4-oxadiazole-2-thione, see: Young & Wood (1955). For metal-assisted transformation of N-benzoyldithiocarbazate to 5-phenyl-1,3,4-oxadiazole-2-thiol (pot) in the presence of ethylenediamine, and its first-row transition-metal complexes, see: Tripathi et al. (2007). For ZnII and CdII metal-organic polymers with a versatile building block 5-(4-pyridyl)-1,3,4-oxadiazole-2-thiol, see: Du et al. (2006).

Experimental top

5-(4-pyridyl)-1,3,4-oxadiazole-2-thione was synthesized according to the reported method (Young & Wood, 1955). The sodium(I) salt of the ligand 2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-ylthio)acetic acid (HPOA) was synthesized as the following process. To a solution of sodium hydroxide (1.60 g, 40 mmol) and 95% alcohol (50 ml) was added 5-pyridyl-2-mercapto-1,3,4-oxadiazole (3.58 g, 20 mmol) and the resulting mixture was refluxed for half an hour. And then a solution of chloroactic acid (1.89 g, 20 mmol) and 95% alcohol (70 ml) was dropwise added to the mixture with continuous refluxing for 3 h. Pale yellow precipitate was filtered. After recrystallized from alcohol/water (2:1), the obtained pure product was 2.76 g. Yield: 51%. Selected IR (cm-1, KBr pellet): 3489(w), 1598(s), 1464(m), 1402(s), 1220(m), 1190(m), 1084(m), 909(m), 835(m), 704(w), 519(m).

The title compound (1), was prepared according to the following process. A mixture of NaPOA (51.8 mg, 0.2 mmol), FeSO4.7H2O (27.8 mg, 0.1 mmol) and deionized water (20 ml) was stirred for 30 minutes and then filtered. The filtrate was allowed to evaporate at room temperature for three days, and yellow crystals were obtain in 36% yield. Selected IR (cm-1, KBr pellet): 3416(m), 3194(m), 1618(s), 1545(s), 1495(w), 1450(s), 1423(w), 1379(s), 1226(m), 1198(m), 1087(w), 1063(w), 1003(w), 871(w), 840(w), 799(w), 743(w), 707(s), 586(w), 522(w).

Refinement top

The H atoms of water molecules were located from difference Fourier maps, and their positional and isotropic displacement parameters were refined, while the other hydrogen atoms were assigned with common isotropic displacement factors [Uiso(H) = 1.2 times Ueq(C)] and included in the final refinement by using geometrical restraints.

Structure description top

Recently, pyridyl-containing 1,3,4-oxadiazole-2-thione have been systematically explored as promising bridging ligands in coordination chemistry. Metal- assisted transformation of N-benzoyldithiocarbazate to 5-phenyl-1,3,4-oxadiazole-2-thiol (pot) in the presence of ethylenediamine, and its first row transition metal complexes were discussed by N. K. Singh and coworkers [Tripathi et al., (2007)]. A report describing ZnII and CdII metal-organic polymers with a versatile building block 5-(4-pyridyl) -1,3,4-oxadiazole-2-thiol was presented by Du et al., (2006). We purposedly engrafted the carboxylic group into the 5-(pyridin-4-yl)-1,3,4-oxadiazol-2-ylthio backbone and synthesized the multifunctional ligands 2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-ylthio)acetic acid (HPOA). Herein we report that the reaction of FeSO4.7H2O and sodium(I) salt of HPOA leads to a new complex [Fe(POA)2(H2O)4] (Fig.1).

The title compound is a mononuclear complex in which every FeII ion located at the inversion center i reproduces the whole molecule through the asymmetry unit consisting of one-half FeII, one deprotonated POA and two water molecules. In (1) the iron(II) center is ligated by four O from water molecules in the equatorial plane, and two POA anions acting as monodentate ligands and occupy the axial positions through their pyridyl nitrogen atoms coordinating to FeII, which is in an axial-elongated octahedral coordination sphere with the bond distances of Fe—O and Fe—N ranging from 2.0605 (17) to 2.2359 (18) Å (Table 1).

In (1) the uncoordinated carboxyl groups as typical hydrogen-bonding acceptors are authentically interesting in the construction of an intricate three-dimensional supramolecular network. Clearly, further aggregation of the monomers (1) is directed by the multiple hydrogen-bonding between the coordinated water donors and the uncoordinated carboxyl acceptors. Fig. 2 shows the complicated hydrogen-bonding system among monomers (1): each coordination water molecule in one monomer forms two O—H···O hydrogen bonds (Table 2) with carboxyl groups to bridge two monomers, while every carboxyl group of POA in the monomer acts as a three-connected hydrogen-bonding acceptor and adopts two different hydrogen-bonding models (bridging and chelating modes) to links with three monomers. Consequently, every monomer acts as a novel six-connected supramolecular synthon to connect with six adjacent monomers. In this way monomers (1) are arrayed to create a three-dimensional supramolecular architecture as shown in Fig. 3.

For the synthesis of 5-(4-pyridyl)-1,3,4-oxadiazole-2-thione, see: Young & Wood (1955). For metal-assisted transformation of N-benzoyldithiocarbazate to 5-phenyl-1,3,4-oxadiazole-2-thiol (pot) in the presence of ethylenediamine, and its first-row transition-metal complexes, see: Tripathi et al. (2007). For ZnII and CdII metal-organic polymers with a versatile building block 5-(4-pyridyl)-1,3,4-oxadiazole-2-thiol, see: Du et al. (2006).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of (1) with atom numbering scheme showing coordination sphere of metal center FeII (30% probability ellipsoids for all non-hydrogen atoms). Symmetry code A: -x, -y + 1, -z.
[Figure 2] Fig. 2. View of a section of the hydrogen-bonding system among monomers (1).
[Figure 3] Fig. 3. View of three-dimensional hydrogen-bonding supramolecular network.
Tetraaquabis(2-{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetato) iron(II) top
Crystal data top
[Fe(C9H6N3O3S)2(H2O)4]F(000) = 616
Mr = 600.37Dx = 1.713 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3319 reflections
a = 14.365 (3) Åθ = 2.4–30.9°
b = 10.709 (2) ŵ = 0.90 mm−1
c = 7.5709 (15) ÅT = 293 K
β = 91.45 (3)°Prism, yellow
V = 1164.2 (4) Å30.20 × 0.20 × 0.20 mm
Z = 2
Data collection top
Siemens SMART CCD
diffractometer		2285 independent reflections
Radiation source: fine-focus sealed tube2179 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scanθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.949, Tmax = 1.000k = −13→13
12366 measured reflectionsl = −9→9
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: inferred from neighbouring sites
wR(F2) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0327P)2 + 0.5694P]
where P = (Fo2 + 2Fc2)/3
2285 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
[Fe(C9H6N3O3S)2(H2O)4]V = 1164.2 (4) Å3
Mr = 600.37Z = 2
Monoclinic, P21/cMo Kα radiation
a = 14.365 (3) ŵ = 0.90 mm−1
b = 10.709 (2) ÅT = 293 K
c = 7.5709 (15) Å0.20 × 0.20 × 0.20 mm
β = 91.45 (3)°
Data collection top
Siemens SMART CCD
diffractometer		2285 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2179 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 1.000Rint = 0.034
12366 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.33 e Å−3
2285 reflectionsΔρmin = −0.25 e Å−3
185 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
Fe10.00000.50000.00000.02246 (14)
S10.65085 (4)0.54011 (6)0.38712 (8)0.03380 (17)
O10.03673 (11)0.31754 (16)0.0529 (3)0.0319 (4)
O2−0.01063 (14)0.52700 (19)0.2780 (2)0.0397 (5)
O30.48086 (10)0.57082 (15)0.2519 (2)0.0302 (4)
O40.84192 (11)0.52207 (17)0.5162 (2)0.0407 (4)
O50.84840 (11)0.70106 (16)0.6691 (2)0.0397 (4)
N10.14562 (12)0.57012 (18)0.0402 (2)0.0272 (4)
N20.44244 (13)0.76466 (19)0.3170 (3)0.0381 (5)
N30.53408 (13)0.74249 (19)0.3821 (3)0.0378 (5)
C10.21910 (15)0.4960 (2)0.0133 (3)0.0281 (5)
H10.20930.4211−0.05160.034*
C20.30836 (15)0.5226 (2)0.0746 (3)0.0298 (5)
H20.35820.46650.05440.036*
C30.16251 (15)0.6786 (2)0.1237 (3)0.0329 (5)
H30.11190.73410.13980.039*
C40.24920 (15)0.7138 (2)0.1873 (3)0.0331 (5)
H40.25800.79200.24460.040*
C50.32349 (14)0.6327 (2)0.1658 (3)0.0259 (5)
C60.41495 (14)0.6630 (2)0.2443 (3)0.0277 (5)
C70.55192 (14)0.6288 (2)0.3411 (3)0.0288 (5)
C80.70959 (16)0.6582 (2)0.5169 (3)0.0367 (6)
H8A0.71160.73660.44780.044*
H8B0.67360.67470.62430.044*
C90.80811 (15)0.6208 (2)0.5712 (3)0.0312 (5)
H2A0.037 (2)0.516 (3)0.338 (4)0.053 (9)*
H2B−0.056 (3)0.522 (3)0.346 (5)0.068 (11)*
H1A0.067 (2)0.281 (3)−0.024 (4)0.051 (9)*
H1B0.070 (2)0.312 (3)0.145 (5)0.066 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0168 (2)0.0266 (2)0.0237 (2)0.00109 (17)−0.00395 (17)0.00006 (17)
S10.0217 (3)0.0386 (3)0.0406 (4)0.0032 (2)−0.0081 (2)−0.0074 (3)
O10.0271 (9)0.0336 (9)0.0345 (10)0.0056 (7)−0.0080 (8)0.0003 (8)
O20.0267 (9)0.0674 (13)0.0250 (9)0.0050 (9)−0.0024 (8)−0.0034 (8)
O30.0180 (8)0.0341 (9)0.0380 (9)−0.0009 (6)−0.0067 (7)−0.0049 (7)
O40.0249 (9)0.0502 (11)0.0468 (11)0.0041 (8)−0.0009 (8)0.0008 (9)
O50.0322 (9)0.0462 (10)0.0399 (10)−0.0095 (8)−0.0174 (8)0.0072 (8)
N10.0174 (9)0.0328 (11)0.0311 (10)−0.0016 (8)−0.0037 (8)0.0004 (8)
N20.0216 (10)0.0379 (12)0.0539 (13)0.0011 (8)−0.0125 (9)−0.0074 (10)
N30.0223 (10)0.0368 (12)0.0536 (13)0.0004 (8)−0.0136 (9)−0.0090 (10)
C10.0229 (11)0.0314 (12)0.0298 (11)−0.0027 (9)−0.0001 (9)−0.0026 (9)
C20.0191 (11)0.0351 (13)0.0352 (12)0.0029 (9)−0.0010 (9)−0.0024 (10)
C30.0209 (11)0.0311 (12)0.0464 (14)0.0024 (9)−0.0052 (10)−0.0042 (11)
C40.0267 (12)0.0297 (12)0.0425 (14)−0.0005 (10)−0.0043 (10)−0.0050 (10)
C50.0176 (10)0.0337 (12)0.0262 (11)−0.0044 (9)−0.0036 (9)0.0042 (9)
C60.0177 (10)0.0338 (13)0.0315 (12)0.0011 (9)−0.0012 (9)0.0009 (10)
C70.0184 (10)0.0376 (13)0.0302 (12)−0.0044 (9)−0.0041 (9)−0.0014 (10)
C80.0270 (12)0.0391 (14)0.0433 (14)−0.0001 (10)−0.0134 (11)−0.0039 (11)
C90.0230 (11)0.0401 (14)0.0303 (12)−0.0037 (10)−0.0028 (9)0.0108 (11)
Geometric parameters (Å, º) top
Fe1—O1i2.0605 (17)N1—C31.341 (3)
Fe1—O12.0605 (17)N2—C61.278 (3)
Fe1—O22.1340 (18)N2—N31.414 (3)
Fe1—O2i2.1340 (18)N3—C71.284 (3)
Fe1—N1i2.2359 (18)C1—C21.382 (3)
Fe1—N12.2359 (18)C1—H10.9500
S1—C71.737 (2)C2—C51.381 (3)
S1—C81.799 (2)C2—H20.9500
O1—H1A0.83 (3)C3—C41.377 (3)
O1—H1B0.83 (3)C3—H30.9500
O2—H2A0.82 (3)C4—C51.389 (3)
O2—H2B0.84 (4)C4—H40.9500
O3—C71.360 (2)C5—C61.464 (3)
O3—C61.368 (3)C8—C91.517 (3)
O4—C91.240 (3)C8—H8A0.9900
O5—C91.265 (3)C8—H8B0.9900
N1—C11.340 (3)
O1i—Fe1—O1180.0N1—C1—H1118.2
O1i—Fe1—O292.22 (8)C2—C1—H1118.2
O1—Fe1—O287.78 (8)C5—C2—C1118.5 (2)
O1i—Fe1—O2i87.78 (8)C5—C2—H2120.8
O1—Fe1—O2i92.22 (8)C1—C2—H2120.8
O2—Fe1—O2i180.00 (11)N1—C3—C4123.6 (2)
O1i—Fe1—N1i93.33 (7)N1—C3—H3118.2
O1—Fe1—N1i86.67 (7)C4—C3—H3118.2
O2—Fe1—N1i95.14 (8)C3—C4—C5118.6 (2)
O2i—Fe1—N1i84.86 (8)C3—C4—H4120.7
O1i—Fe1—N186.67 (7)C5—C4—H4120.7
O1—Fe1—N193.33 (7)C2—C5—C4118.74 (19)
O2—Fe1—N184.86 (8)C2—C5—C6121.4 (2)
O2i—Fe1—N195.14 (8)C4—C5—C6119.9 (2)
N1i—Fe1—N1180.0N2—C6—O3112.99 (18)
C7—S1—C895.46 (11)N2—C6—C5128.9 (2)
Fe1—O1—H1A116 (2)O3—C6—C5118.03 (19)
Fe1—O1—H1B112 (2)N3—C7—O3113.64 (19)
H1A—O1—H1B105 (3)N3—C7—S1129.59 (17)
Fe1—O2—H2A116 (2)O3—C7—S1116.75 (17)
Fe1—O2—H2B132 (2)C9—C8—S1112.55 (17)
H2A—O2—H2B108 (3)C9—C8—H8A109.1
C7—O3—C6101.62 (17)S1—C8—H8A109.1
C1—N1—C3116.77 (19)C9—C8—H8B109.1
C1—N1—Fe1121.21 (15)S1—C8—H8B109.1
C3—N1—Fe1120.82 (15)H8A—C8—H8B107.8
C6—N2—N3106.39 (19)O4—C9—O5126.8 (2)
C7—N3—N2105.35 (18)O4—C9—C8120.3 (2)
N1—C1—C2123.7 (2)O5—C9—C8112.9 (2)
O1i—Fe1—N1—C1−152.98 (18)C3—C4—C5—C22.9 (3)
O1—Fe1—N1—C127.02 (18)C3—C4—C5—C6−175.1 (2)
O2—Fe1—N1—C1114.48 (18)N3—N2—C6—O3−0.5 (3)
O2i—Fe1—N1—C1−65.52 (18)N3—N2—C6—C5175.9 (2)
N1i—Fe1—N1—C17 (44)C7—O3—C6—N20.8 (3)
O1i—Fe1—N1—C339.94 (18)C7—O3—C6—C5−176.01 (19)
O1—Fe1—N1—C3−140.06 (18)C2—C5—C6—N2172.6 (2)
O2—Fe1—N1—C3−52.59 (18)C4—C5—C6—N2−9.4 (4)
O2i—Fe1—N1—C3127.41 (18)C2—C5—C6—O3−11.1 (3)
N1i—Fe1—N1—C3−161 (44)C4—C5—C6—O3166.9 (2)
C6—N2—N3—C70.0 (3)N2—N3—C7—O30.6 (3)
C3—N1—C1—C23.6 (3)N2—N3—C7—S1−177.87 (18)
Fe1—N1—C1—C2−164.01 (18)C6—O3—C7—N3−0.8 (3)
N1—C1—C2—C5−1.3 (4)C6—O3—C7—S1177.81 (15)
C1—N1—C3—C4−2.6 (3)C8—S1—C7—N33.4 (3)
Fe1—N1—C3—C4165.05 (19)C8—S1—C7—O3−174.96 (18)
N1—C3—C4—C5−0.6 (4)C7—S1—C8—C9−174.28 (18)
C1—C2—C5—C4−2.0 (3)S1—C8—C9—O44.8 (3)
C1—C2—C5—C6176.0 (2)S1—C8—C9—O5−177.06 (17)
Symmetry code: (i) −x, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O5ii0.83 (3)1.87 (3)2.691 (3)170 (3)
O1—H1B···O5iii0.83 (3)1.82 (4)2.649 (2)174 (3)
O2—H2A···O4iii0.82 (3)2.07 (3)2.896 (3)177 (3)
O2—H2B···O4iv0.84 (4)1.98 (4)2.817 (3)175 (3)
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula[Fe(C9H6N3O3S)2(H2O)4]
Mr600.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.365 (3), 10.709 (2), 7.5709 (15)
β (°) 91.45 (3)
V (Å3)1164.2 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.90
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerSiemens SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.949, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		12366, 2285, 2179
Rint0.034
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.078, 1.13
No. of reflections2285
No. of parameters185
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.25

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Fe1—O12.0605 (17)Fe1—N12.2359 (18)
Fe1—O22.1340 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O5i0.83 (3)1.87 (3)2.691 (3)170 (3)
O1—H1B···O5ii0.83 (3)1.82 (4)2.649 (2)174 (3)
O2—H2A···O4ii0.82 (3)2.07 (3)2.896 (3)177 (3)
O2—H2B···O4iii0.84 (4)1.98 (4)2.817 (3)175 (3)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.
 

Acknowledgements

This work was supported by the Natural Science Foundation of China.

References

First citationDu, M., Zhang, Z. H., Zhao, X.-J. & Xu, Q. (2006). Inorg. Chem. 45, 5785–5792.  Web of Science CSD CrossRef PubMed 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 citationSiemens (1994). SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSiemens (1996). SMART. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationTripathi, P., Pal, A., Jancik, V., Pandey, A. K., Singh, J. & Singh, N. K. (2007). Polyhedron, 26, 2597–2602.  Web of Science CSD CrossRef CAS Google Scholar
 First citationYoung, R. W. & Wood, K. H. (1955). J. Am. Chem. Soc. 77, 400–403.  CrossRef CAS Web of Science Google Scholar

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page m1457
https://doi.org/10.1107/S1600536811038918
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