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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m276–m277.
Published online 2008 January 4. doi:  10.1107/S1600536807064860
PMCID: PMC2960379

catena-Poly[[tetra­aqua­zinc(II)]-μ-2,2′-dihydr­oxy-5,5′-diazenediyldibenzoato]

Abstract

In the title compound, [Zn(C14H8N2O6)(H2O)4]n, the 2,2′-dihydr­oxy-5,5′-diazenediyldibenzoate ligand acts as a carboxyl­ate bridge, leading to the formation of a polymeric chain running along the [1An external file that holds a picture, illustration, etc.
Object name is e-64-0m276-efi1.jpg0] direction. The ZnII atom is hexa-coordinated in a distorted octa­hedral geometry by six O atoms [Zn—O = 2.055 (4)–2.132 (3) Å] from two carboxylate ligands and four water mol­ecules. The crystal packing is stabilized by inter­molecular O—H(...)O, O—H(...)N and C—H(...)O hydrogen bonds, and two π–π inter­actions. The centroid–centroid distances are 3.803 (16) and 3.804 (17) Å.

Related literature

For related literature, see: Klotz (2005 [triangle]); Tang, Tan & Cao (2007 [triangle]); Tang, Tan, Chen & Cao (2007 [triangle]); Tang, Yang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m276-scheme1.jpg

Experimental

Crystal data

  • [Zn(C14H8N2O6)(H2O)4]
  • M r = 437.66
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m276-efi2.jpg
  • a = 9.510 (2) Å
  • b = 11.255 (3) Å
  • c = 16.214 (4) Å
  • β = 107.019 (3)°
  • V = 1659.5 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.54 mm−1
  • T = 296 (2) K
  • 0.25 × 0.22 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.699, T max = 0.861
  • 10784 measured reflections
  • 3278 independent reflections
  • 3036 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.098
  • S = 1.10
  • 3278 reflections
  • 277 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.70 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2000 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064860/is2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064860/is2258Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Gannan Medical University Master Development Foundation.

supplementary crystallographic information

Comment

Olsalazine, 2,2'-dihydroxy-5,5'-diazenediyldibenzoic acid, has been widely used to prevent and treat the inflammatory bowel diseases, such as ulcerative colitis (Klotz, 2005). In previous work, we have synthesized a serial of Zn (Tang, Tan, Chen & Cao, 2007), Cd and Co (Tang, Yang et al., 2007) complexes with phenanthroline as auxiliary ligand. We have also reported a Mn complex of olsalazine (Tang, Tan & Cao, 2007), but the zinc complex with single olsalazine as building block has not been reported yet. Here we reported the crystal structure of the title compound, (I), a new zinc complex of olsalazine.

In (I), the Zn atom is hexa-coordinated (Fig. 1) by two O atoms from two L ligands [H2L=3,3-azo-bis(6-hydroxybenzoic acid)] and four water molecules in a distorted octahedral geometry (Table 1). Two ligands are cis to each other in an octahedral environment. Each ligand L acts as a carboxylate bridge, which leads to formation of a polymeric chain running in the direction [110]. Two neighbouring polymeric chains are paired by π···π interactions between the aromatic rings; the distances Cg1···Cg1i and Cg2···Cg2i are 3.803 (16) and 3.804 (17) Å, respectively [Cg1 and Cg2 are centroids of C2—C7 and C8—C13 rings, respectively; symmetry code: (i) x - 1, y - 1, z]. The crystal packing is further stabilized by the intermolecular O—H···O, O—H···N and C—H···O hydrogen bonds (Table 2).

Refinement

The hydroxy and C-bound H atoms were placed in calculated positions (C—H = 0.93 Å and O—H = 0.82 Å) and included in the refinement in the riding-model approximation, with Uiso(H) = 1.2Ueq(C,O). The water H atoms were located in a difference Fourier map and refined isotropically.

Figures

Fig. 1.
A part of the polymeric structure of (I), showing displacement ellipsoids drawn at the 30% probability level and the atomic labelling. Unlabelled atoms are related to labelled atoms by the symmetry code (x - 1, y + 1, z).

Crystal data

[Zn(C14H8N2O6)(H2O)4]F000 = 896
Mr = 437.66Dx = 1.752 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 935 reflections
a = 9.510 (2) Åθ = 1.8–26.0º
b = 11.255 (3) ŵ = 1.54 mm1
c = 16.214 (4) ÅT = 296 (2) K
β = 107.019 (3)ºBlock, orange
V = 1659.5 (7) Å30.25 × 0.22 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer3278 independent reflections
Radiation source: fine-focus sealed tube3036 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.034
T = 296(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −11→11
Tmin = 0.699, Tmax = 0.861k = −13→13
10784 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098  w = 1/[σ2(Fo2) + (0.0307P)2 + 1.3308P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3278 reflectionsΔρmax = 0.39 e Å3
277 parametersΔρmin = −0.70 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Zn10.71408 (5)0.64023 (4)0.21196 (3)0.03166 (13)
O60.9487 (4)0.4284 (3)0.2011 (2)0.0620 (11)
O50.7705 (4)0.5388 (3)0.1179 (2)0.0434 (8)
O40.6849 (4)0.5057 (3)−0.0439 (2)0.0511 (9)
H4A0.68730.53590.00250.077*
O31.5187 (4)−0.2597 (3)−0.0536 (2)0.0570 (10)
H3A1.5603−0.2816−0.00420.085*
O21.5791 (3)−0.2637 (2)0.10891 (19)0.0375 (7)
O11.4725 (4)−0.1395 (3)0.17841 (18)0.0508 (8)
O4W0.5362 (4)0.5313 (3)0.2060 (3)0.0535 (9)
O3W0.8865 (4)0.7510 (3)0.2132 (3)0.0501 (8)
O2W0.6659 (4)0.7520 (3)0.3064 (2)0.0493 (9)
O1W0.8398 (4)0.5403 (3)0.3147 (2)0.0431 (8)
N21.0930 (4)0.1421 (3)0.0030 (2)0.0343 (7)
N11.1233 (4)0.1052 (3)−0.0637 (2)0.0334 (8)
C140.8672 (5)0.4557 (4)0.1291 (3)0.0402 (11)
C130.8783 (5)0.3916 (3)0.0511 (3)0.0335 (9)
C120.7874 (5)0.4192 (4)−0.0312 (3)0.0343 (9)
C110.7972 (5)0.3553 (4)−0.1026 (3)0.0414 (10)
H11A0.73670.3751−0.15710.050*
C100.8949 (5)0.2633 (4)−0.0935 (3)0.0372 (9)
H10A0.89890.2196−0.14140.045*
C90.9877 (5)0.2357 (3)−0.0127 (3)0.0316 (9)
C80.9781 (5)0.2998 (4)0.0582 (3)0.0370 (10)
H8A1.04060.28070.11230.044*
C71.2236 (4)0.0099 (3)−0.0537 (3)0.0322 (9)
C61.2416 (5)−0.0349 (4)−0.1298 (3)0.0396 (10)
H6A1.1871−0.0025−0.18220.048*
C51.3378 (6)−0.1259 (4)−0.1296 (3)0.0473 (12)
H5A1.3469−0.1558−0.18120.057*
C41.4210 (5)−0.1727 (4)−0.0517 (3)0.0372 (10)
C31.4032 (4)−0.1293 (4)0.0259 (2)0.0301 (8)
C21.3051 (5)−0.0383 (3)0.0244 (3)0.0316 (9)
H2A1.2936−0.00930.07580.038*
C11.4901 (5)−0.1794 (4)0.1108 (3)0.0321 (9)
H1WA0.872 (6)0.496 (5)0.283 (4)0.062 (18)*
H3WA0.872 (7)0.779 (5)0.170 (4)0.05 (2)*
H4WA0.507 (9)0.504 (6)0.159 (5)0.09 (3)*
H2WA0.597 (7)0.802 (5)0.260 (4)0.073 (19)*
H3WB0.921 (7)0.796 (6)0.250 (5)0.07 (2)*
H4WB0.545 (7)0.488 (5)0.253 (4)0.066 (19)*
H1WB0.895 (8)0.580 (6)0.359 (4)0.08 (2)*
H2WB0.619 (8)0.703 (6)0.330 (5)0.09 (3)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0368 (2)0.0289 (2)0.0260 (2)0.0034 (2)0.00388 (19)0.0022 (2)
O60.076 (2)0.070 (2)0.0266 (18)0.045 (2)−0.0057 (17)−0.0064 (16)
O50.0494 (18)0.0396 (16)0.0341 (18)0.0196 (14)0.0009 (13)−0.0061 (13)
O40.056 (2)0.0503 (18)0.0372 (19)0.0296 (16)−0.0021 (15)−0.0070 (15)
O30.076 (2)0.062 (2)0.0339 (19)0.0451 (19)0.0164 (18)0.0057 (16)
O20.0453 (16)0.0341 (14)0.0297 (16)0.0143 (13)0.0057 (13)0.0039 (12)
O10.068 (2)0.0524 (16)0.0286 (15)0.0272 (18)0.0085 (16)0.0010 (16)
O4W0.051 (2)0.059 (2)0.039 (2)−0.0120 (16)−0.0032 (17)0.0131 (19)
O3W0.060 (2)0.055 (2)0.030 (2)−0.0195 (17)0.0066 (17)0.001 (2)
O2W0.061 (2)0.051 (2)0.034 (2)0.0169 (18)0.0105 (16)0.0009 (15)
O1W0.0504 (19)0.0440 (17)0.0321 (19)0.0105 (15)0.0077 (14)0.0042 (14)
N20.0380 (17)0.0340 (15)0.0279 (17)0.0107 (16)0.0052 (14)0.0014 (16)
N10.0393 (18)0.0326 (17)0.0265 (18)0.0100 (14)0.0070 (15)0.0019 (13)
C140.044 (2)0.037 (2)0.036 (3)0.0115 (19)0.0051 (19)−0.0071 (19)
C130.039 (2)0.0294 (19)0.026 (2)0.0077 (17)−0.0003 (18)−0.0018 (15)
C120.032 (2)0.034 (2)0.032 (2)0.0076 (18)0.0013 (16)0.0019 (18)
C110.042 (2)0.048 (2)0.027 (2)0.014 (2)−0.0004 (18)0.000 (2)
C100.047 (2)0.039 (2)0.023 (2)0.0071 (19)0.0049 (17)−0.0056 (17)
C90.035 (2)0.0302 (19)0.028 (2)0.0089 (16)0.0061 (17)−0.0002 (16)
C80.043 (2)0.037 (2)0.026 (2)0.0108 (19)0.0030 (18)−0.0017 (18)
C70.035 (2)0.0308 (19)0.029 (2)0.0071 (16)0.0067 (17)0.0030 (17)
C60.047 (3)0.040 (2)0.026 (2)0.015 (2)0.0027 (18)0.0056 (18)
C50.068 (3)0.049 (2)0.023 (2)0.020 (3)0.009 (2)−0.001 (2)
C40.046 (2)0.034 (2)0.031 (2)0.0162 (18)0.0108 (19)0.0018 (17)
C30.035 (2)0.0271 (17)0.0262 (19)0.0065 (17)0.0064 (16)0.0032 (17)
C20.035 (2)0.0306 (19)0.029 (2)0.0051 (17)0.0088 (17)−0.0001 (17)
C10.036 (2)0.0322 (19)0.026 (2)0.0039 (17)0.0059 (17)−0.0014 (16)

Geometric parameters (Å, °)

Zn1—O3W2.055 (4)N2—N11.267 (5)
Zn1—O4W2.069 (4)N2—C91.425 (5)
Zn1—O1W2.075 (3)N1—C71.413 (5)
Zn1—O2i2.086 (3)C14—C131.487 (6)
Zn1—O52.097 (3)C13—C81.385 (6)
Zn1—O2W2.132 (3)C13—C121.396 (6)
O6—C141.236 (6)C12—C111.389 (6)
O5—C141.286 (5)C11—C101.370 (6)
O4—C121.350 (5)C11—H11A0.9300
O4—H4A0.8200C10—C91.383 (6)
O3—C41.356 (5)C10—H10A0.9300
O3—H3A0.8200C9—C81.383 (6)
O2—C11.278 (5)C8—H8A0.9300
O2—Zn1ii2.086 (3)C7—C21.387 (6)
O1—C11.240 (5)C7—C61.389 (6)
O4W—H4WA0.80 (8)C6—C51.372 (6)
O4W—H4WB0.88 (7)C6—H6A0.9300
O3W—H3WA0.74 (6)C5—C41.382 (6)
O3W—H3WB0.78 (7)C5—H5A0.9300
O2W—H2WA1.02 (7)C4—C31.406 (6)
O2W—H2WB0.87 (7)C3—C21.381 (5)
O1W—H1WA0.83 (6)C3—C11.493 (5)
O1W—H1WB0.88 (7)C2—H2A0.9300
O3W—Zn1—O4W177.75 (16)C12—C13—C14121.8 (4)
O3W—Zn1—O1W92.90 (16)O4—C12—C11117.9 (4)
O4W—Zn1—O1W89.28 (15)O4—C12—C13121.6 (4)
O3W—Zn1—O2i89.72 (15)C11—C12—C13120.5 (4)
O4W—Zn1—O2i88.10 (14)C10—C11—C12120.7 (4)
O1W—Zn1—O2i177.36 (13)C10—C11—H11A119.7
O3W—Zn1—O587.93 (16)C12—C11—H11A119.7
O4W—Zn1—O591.35 (16)C11—C10—C9119.8 (4)
O1W—Zn1—O594.52 (13)C11—C10—H10A120.1
O2i—Zn1—O585.89 (11)C9—C10—H10A120.1
O3W—Zn1—O2W88.49 (17)C8—C9—C10119.4 (4)
O4W—Zn1—O2W92.21 (18)C8—C9—N2116.8 (4)
O1W—Zn1—O2W86.44 (15)C10—C9—N2123.8 (4)
O2i—Zn1—O2W93.32 (13)C9—C8—C13122.0 (4)
O5—Zn1—O2W176.33 (15)C9—C8—H8A119.0
C14—O5—Zn1128.2 (3)C13—C8—H8A119.0
C12—O4—H4A109.5C2—C7—C6119.2 (4)
C4—O3—H3A109.5C2—C7—N1125.4 (4)
C1—O2—Zn1ii128.5 (3)C6—C7—N1115.4 (3)
Zn1—O4W—H4WA109 (6)C5—C6—C7121.6 (4)
Zn1—O4W—H4WB114 (4)C5—C6—H6A119.2
H4WA—O4W—H4WB122 (6)C7—C6—H6A119.2
Zn1—O3W—H3WA109 (5)C6—C5—C4119.3 (4)
Zn1—O3W—H3WB125 (5)C6—C5—H5A120.3
H3WA—O3W—H3WB111 (7)C4—C5—H5A120.3
Zn1—O2W—H2WA91 (3)O3—C4—C5117.9 (4)
Zn1—O2W—H2WB101 (5)O3—C4—C3122.2 (4)
H2WA—O2W—H2WB112 (5)C5—C4—C3119.9 (4)
Zn1—O1W—H1WA93 (4)C2—C3—C4120.0 (3)
Zn1—O1W—H1WB117 (4)C2—C3—C1119.0 (4)
H1WA—O1W—H1WB125 (6)C4—C3—C1121.0 (4)
N1—N2—C9114.4 (3)C3—C2—C7120.0 (4)
N2—N1—C7117.7 (3)C3—C2—H2A120.0
O6—C14—O5122.6 (4)C7—C2—H2A120.0
O6—C14—C13120.1 (4)O1—C1—O2123.5 (4)
O5—C14—C13117.3 (4)O1—C1—C3119.8 (4)
C8—C13—C12117.6 (4)O2—C1—C3116.7 (4)
C8—C13—C14120.6 (4)

Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y−1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O60.84 (6)1.86 (6)2.677 (5)168 (6)
O1W—H1WB···N2iii0.88 (7)2.32 (6)3.058 (5)143 (6)
O2W—H2WA···O1i1.01 (6)1.63 (6)2.636 (5)170 (6)
O2W—H2WB···O3iv0.87 (7)2.44 (8)2.997 (5)123 (6)
O3W—H3WA···N1v0.74 (6)2.17 (6)2.893 (5)164 (5)
O3W—H3WB···O6iii0.78 (8)1.95 (7)2.664 (5)152 (7)
O4W—H4WA···O4vi0.79 (7)2.20 (8)2.875 (6)144 (8)
O4W—H4WB···O1iii0.89 (6)1.85 (6)2.703 (5)160 (6)
O3—H3A···O20.821.802.528 (4)147
O4—H4A···O50.821.812.537 (4)148
C2—H2A···O1Wvii0.932.533.405 (6)157

Symmetry codes: (iii) −x+2, y+1/2, −z+1/2; (i) x−1, y+1, z; (iv) x−1, −y+1/2, z+1/2; (v) −x+2, −y+1, −z; (vi) −x+1, −y+1, −z; (vii) −x+2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2258).

References

  • Bruker (2000). SMART, SAINT, SHELXTL and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Klotz, U. (2005). Dig. Liver Dis.37, 381–388. [PubMed]
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Tang, Y.-Z., Tan, Y.-H. & Cao, Y.-W. (2007). Acta Cryst. E63, m1175–m1176.
  • Tang, Y.-Z., Tan, Y.-H., Chen, S.-H. & Cao, Y.-W. (2007). Z. Anorg. Allg. Chem.633, 332–335.
  • Tang, Y.-Z., Yang, S.-P., Tan, Y.-H., Chen, S.-H., Cao, Y.-W. & Wang, P. (2007). Wuji Huaxue Xuebao (Chin. J. Inorg. Chem.), 23, 70–74.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography