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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 12| December 2011| Pages m1701-m1702
https://doi.org/10.1107/S1600536811045156

Tetra­aqua­bis­­[1-(3-carb­­oxy­phen­yl)-4,4′-bipyridin-1-ium-κN1′]zinc bis­­(4,5-carb­­oxy­benzene-1,2-di­carboxyl­ate) 2.5-hydrate

Jie Zhang,a Yi Tana and Zhiyong Fua*

aKey Lab for Fuel Cell Technology of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, People's Republic of China
*Correspondence e-mail: zyfu@scut.edu.cn

(Received 23 August 2011; accepted 27 October 2011; online 5 November 2011)

In the complex cation of the title compound, [Zn(C17H13N2O2)2(H2O)4](C10H4O8)2·2.5H2O, the ZnII atom, lying on an inversion center, is coordinated by two N atoms from two N-(3-carb­oxy­phen­yl)-4,4′-bipyridin-1-ium ligands and four water mol­ecules in a distorted octa­hedral geometry. The pyromellitate anion is double deprotonated. O—H⋯O and C—H⋯O hydrogen bonds connect the cations, anions and uncoordinated water mol­ecules into a three-dimensional supra­molecular network. One of the two lattice water molecules shows an occupancy of 0.25. An intra­molecular O—H⋯O hydrogen bond is present in the anion.

Related literature

For background to the structures and applications of viologen compounds, see: Ebbesen et al. (1984[Ebbesen, T. W., Manring, L. E. & Peters, K. S. (1984). J. Am. Chem. Soc. 106, 7400-7404.]); Jin et al. (2010[Jin, X.-H., Sun, J.-K., Xu, X.-M., Li, Z.-H. & Zhang, J. (2010). Chem. Commun. 46, 4695-4697.]); Sun et al. (2005[Sun, Y.-Q., Zhang, J., Ju, Z.-F. & Yang, G.-Y. (2005). Cryst. Growth Des. 5, 1939-1943.]); Xu et al. (2007[Xu, G., Guo, G.-C., Wang, M.-S. & Zhang, Z.-G. (2007). Angew. Chem. Int. Ed. 46, 3249-3251.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C17H13N2O2)2(H2O)4](C10H4O8)2·2.5H2O

  • Mr = 1241.33

  • Monoclinic, P 21 /c

  • a = 7.5476 (2) Å

  • b = 19.5528 (4) Å

  • c = 19.2752 (4) Å

  • β = 110.431 (2)°

  • V = 2665.63 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.56 mm−1

  • T = 298 K

  • 0.43 × 0.41 × 0.37 mm
Data collection

  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.781, Tmax = 0.825

  • 25451 measured reflections

  • 4867 independent reflections

  • 4250 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.078

  • S = 1.06

  • 4867 reflections

  • 429 parameters

  • 4 restraints

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

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H7⋯O12i 0.87 (2) 1.80 (3) 2.656 (3) 164 (3)
O3—H1⋯O11ii 0.85 (2) 1.88 (3) 2.732 (2) 175 (3)
O3—H2⋯O11iii 0.81 (3) 2.03 (2) 2.820 (4) 163 (2)
O4—H3⋯O13iii 0.84 (2) 1.84 (3) 2.677 (6) 175 (3)
O4—H4⋯O12iv 0.90 (3) 1.79 (4) 2.694 (2) 177 (4)
O6—H9⋯O7 0.87 (3) 1.56 (3) 2.418 (2) 174 (3)
O9—H8⋯O8iii 0.85 (3) 1.82 (3) 2.646 (3) 163 (4)
O13—H5⋯O10 0.92 (4) 1.90 (2) 2.813 (3) 174 (3)
O13—H6⋯O7iii 0.87 (4) 1.86 (4) 2.723 (2) 169 (3)
O14—H11⋯O13 0.82 (2) 2.18 (2) 2.846 (2) 138 (2)
C7—H7A⋯O1v 0.93 2.30 3.155 (2) 153
C8—H8A⋯O12vi 0.93 2.52 3.302 (2) 142
C9—H9A⋯O2vii 0.93 2.30 3.225 (2) 172
C10—H10A⋯O5viii 0.93 2.15 3.060 (3) 167
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) [x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) x-1, y, z; (vii) -x+1, -y+2, -z+1; (viii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811045156/hy2468sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045156/hy2468Isup2.hkl

checkCIF report


Comment top

Viologens are quaternary salts derived from 4,4'-bipyridine (Ebbesen et al., 1984). Intensively interests have been focused on these compounds for their electron-transfer properties and enormous potential applications in electrochromic displays and optically switchable devices (Jin et al., 2010; Sun et al., 2005; Xu et al., 2007). Most of them are dimethyl-, diethyl-, dibetaine- and dibenzyl viologens. Here we report the synthesis and structure of a new viologen compound with N-3-carboxyphenyl substitution and double-deprotonated pyromellitate as compensation anions.

The asymmetric unit of the title compound contains one ZnII atom lying on an inversion center, one N-(3-carboxyphenyl)-4,4'-bipyridinium ligand, one double-deprotonated pyromellitate anion, two coordinated water molecules and 1.25 uncooedinated water molecules (Fig. 1). The ZnII atom is six-coordinated by two N atoms of the viologen ligands and four O atoms of water molecules. The Zn—N bond length is 2.1689 (14) Å and the Zn—O bond lengths are 2.0798 (13) and 2.1335 (14) Å. The bond angles vary from 88.98 (6) to 93.42 (5)°, indicating a distorted octahedral geometry. O—H···O and C—H···O hydrogen bonds (Table 1) connect the cations, anions and uncoordinated water molecules into a three-dimensional supramolecular network (Fig. 2).

Related literature top

For background to the structures and applications of viologen compounds, see: Ebbesen et al. (1984); Jin et al. (2010); Sun et al. (2005); Xu et al. (2007).

Experimental top

A mixture of N-(3-carboxyphenyl)-4,4'-bipyridinium chloride (0.2 mmol), ZnO(1 mmol), phosphoric acid (2 mmol), pyromellitic acid (0.2 mmol) and water (5 ml) was sealed in a 23 ml Teflon-lined bomb at 120°C for 72 h. Yellow block-shaped crystals were obtained.

Refinement top

H atoms of the hydroxyl groups and water molecules were located in a difference Fourier map and refined with Uiso(H) = 1.5Ueq(O). H atoms attached to O6 and O14 were refined with a distance restraint of O—H = 0.82 (2) Å and with Uiso(H) = 1.5Ueq(O). Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C).

Structure description top

Viologens are quaternary salts derived from 4,4'-bipyridine (Ebbesen et al., 1984). Intensively interests have been focused on these compounds for their electron-transfer properties and enormous potential applications in electrochromic displays and optically switchable devices (Jin et al., 2010; Sun et al., 2005; Xu et al., 2007). Most of them are dimethyl-, diethyl-, dibetaine- and dibenzyl viologens. Here we report the synthesis and structure of a new viologen compound with N-3-carboxyphenyl substitution and double-deprotonated pyromellitate as compensation anions.

The asymmetric unit of the title compound contains one ZnII atom lying on an inversion center, one N-(3-carboxyphenyl)-4,4'-bipyridinium ligand, one double-deprotonated pyromellitate anion, two coordinated water molecules and 1.25 uncooedinated water molecules (Fig. 1). The ZnII atom is six-coordinated by two N atoms of the viologen ligands and four O atoms of water molecules. The Zn—N bond length is 2.1689 (14) Å and the Zn—O bond lengths are 2.0798 (13) and 2.1335 (14) Å. The bond angles vary from 88.98 (6) to 93.42 (5)°, indicating a distorted octahedral geometry. O—H···O and C—H···O hydrogen bonds (Table 1) connect the cations, anions and uncoordinated water molecules into a three-dimensional supramolecular network (Fig. 2).

For background to the structures and applications of viologen compounds, see: Ebbesen et al. (1984); Jin et al. (2010); Sun et al. (2005); Xu et al. (2007).

Computing details top

Data collection: SMART (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: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (a) 1-x, 1-y, 1-z.]
[Figure 2] Fig. 2. The three-dimensional supramolecular structure of the title compound. Dashed lines denote hydrogen bonds.
Tetraaquabis[1-(3-carboxyphenyl)-4,4'-bipyridin-1-ium-κN1']zinc bis(4,5-carboxybenzene-1,2-dicarboxylate) 2.5-hydrate top
Crystal data top
[Zn(C17H13N2O2)2(H2O)4](C10H4O8)2·2.5H2OF(000) = 1282
Mr = 1241.33Dx = 1.547 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4867 reflections
a = 7.5476 (2) Åθ = 3.1–25.4°
b = 19.5528 (4) ŵ = 0.56 mm−1
c = 19.2752 (4) ÅT = 298 K
β = 110.431 (2)°Block, yellow
V = 2665.63 (10) Å30.43 × 0.41 × 0.37 mm
Z = 2
Data collection top
Bruker APEX CCD
diffractometer		4867 independent reflections
Radiation source: fine-focus sealed tube4250 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→8
Tmin = 0.781, Tmax = 0.825k = −23→23
25451 measured reflectionsl = −23→23
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0331P)2 + 1.443P]
where P = (Fo2 + 2Fc2)/3
4867 reflections(Δ/σ)max = 0.001
429 parametersΔρmax = 0.29 e Å−3
4 restraintsΔρmin = −0.36 e Å−3
Crystal data top
[Zn(C17H13N2O2)2(H2O)4](C10H4O8)2·2.5H2OV = 2665.63 (10) Å3
Mr = 1241.33Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.5476 (2) ŵ = 0.56 mm−1
b = 19.5528 (4) ÅT = 298 K
c = 19.2752 (4) Å0.43 × 0.41 × 0.37 mm
β = 110.431 (2)°
Data collection top
Bruker APEX CCD
diffractometer		4867 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4250 reflections with I > 2σ(I)
Tmin = 0.781, Tmax = 0.825Rint = 0.028
25451 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0314 restraints
wR(F2) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.29 e Å−3
4867 reflectionsΔρmin = −0.36 e Å−3
429 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.50000.50000.50000.02391 (9)
O10.5186 (2)1.24085 (7)0.33078 (8)0.0434 (4)
H70.583 (4)1.2716 (14)0.3626 (15)0.065*
O20.6136 (2)1.16786 (7)0.42474 (8)0.0513 (4)
O30.80086 (19)0.50774 (7)0.53939 (8)0.0327 (3)
H10.844 (3)0.4741 (13)0.5221 (13)0.049*
H20.855 (3)0.5404 (13)0.5307 (13)0.049*
O40.4919 (2)0.53685 (7)0.60006 (8)0.0344 (3)
H30.591 (4)0.5432 (13)0.6368 (14)0.052*
H40.423 (3)0.5747 (13)0.5993 (13)0.052*
O50.7710 (4)0.55277 (9)0.05365 (11)0.0879 (8)
O60.7924 (2)0.53366 (8)−0.05325 (9)0.0507 (4)
H90.819 (4)0.5542 (14)−0.0882 (13)0.076*
O70.8657 (3)0.59789 (8)−0.14700 (9)0.0702 (6)
O80.9161 (2)0.70368 (8)−0.17320 (7)0.0464 (4)
O90.9545 (2)0.74468 (7)0.20592 (7)0.0419 (4)
H80.939 (4)0.7691 (13)0.2399 (15)0.063*
O100.9735 (2)0.84566 (7)0.15526 (8)0.0444 (4)
O111.04737 (18)0.89852 (6)0.00847 (7)0.0349 (3)
O121.29187 (17)0.84798 (6)0.09494 (7)0.0313 (3)
O130.8157 (3)0.95061 (10)0.21503 (10)0.0555 (4)
H50.872 (5)0.9152 (19)0.199 (2)0.105 (13)*
H60.816 (5)0.9357 (17)0.257 (2)0.097 (12)*
O140.8680 (18)1.0750 (5)0.2965 (6)0.109 (3)0.25
H100.91 (3)1.062 (10)0.340 (4)0.163*0.25
H110.798 (10)1.044 (3)0.275 (10)0.163*0.25
N10.4598 (2)0.60196 (7)0.45273 (8)0.0267 (3)
N20.3534 (2)0.93790 (7)0.31154 (8)0.0253 (3)
C10.3529 (3)0.61428 (9)0.38216 (11)0.0359 (4)
H1A0.29410.57750.35250.043*
C20.3255 (3)0.67884 (9)0.35108 (11)0.0360 (4)
H2A0.25280.68480.30140.043*
C30.5401 (3)0.65598 (9)0.49434 (10)0.0299 (4)
H3A0.61670.64850.54330.036*
C40.5151 (3)0.72233 (9)0.46828 (10)0.0301 (4)
H4A0.57020.75840.49990.036*
C50.4079 (2)0.73488 (8)0.39504 (10)0.0253 (4)
C60.3860 (2)0.80580 (9)0.36554 (10)0.0256 (4)
C70.3945 (3)0.81976 (9)0.29649 (10)0.0340 (4)
H7A0.41000.78410.26720.041*
C80.3803 (3)0.88552 (9)0.27086 (10)0.0343 (4)
H8A0.38930.89420.22480.041*
C90.3598 (3)0.86071 (9)0.40711 (10)0.0284 (4)
H9A0.35470.85320.45400.034*
C100.3416 (3)0.92569 (9)0.37883 (10)0.0288 (4)
H10A0.32080.96190.40630.035*
C120.3409 (3)1.00795 (8)0.28392 (10)0.0263 (4)
C130.2324 (3)1.02160 (10)0.21080 (10)0.0355 (4)
H13A0.16840.98660.17930.043*
C140.2213 (3)1.08835 (10)0.18574 (11)0.0407 (5)
H14A0.15041.09830.13670.049*
C150.3149 (3)1.14040 (9)0.23309 (10)0.0330 (4)
H15A0.30521.18520.21600.040*
C160.4233 (3)1.12578 (9)0.30622 (10)0.0261 (4)
C170.4371 (2)1.05870 (9)0.33179 (9)0.0265 (4)
H17A0.51031.04830.38050.032*
C180.5277 (3)1.17943 (9)0.36038 (10)0.0290 (4)
C190.8122 (3)0.57302 (10)0.00281 (12)0.0367 (5)
C200.8992 (3)0.65999 (10)−0.13012 (10)0.0311 (4)
C210.9692 (2)0.78374 (9)0.15265 (10)0.0272 (4)
C221.1268 (2)0.84837 (8)0.04705 (9)0.0240 (4)
C230.8857 (2)0.64591 (9)0.00489 (10)0.0252 (4)
C240.9082 (2)0.67918 (9)0.07170 (9)0.0262 (4)
H24A0.87780.65570.10800.031*
C250.9740 (2)0.74564 (9)0.08605 (9)0.0231 (4)
C261.0261 (2)0.78040 (8)0.03287 (9)0.0223 (3)
C270.9965 (2)0.74906 (9)−0.03482 (9)0.0245 (4)
H27A1.02560.7733−0.07100.029*
C280.9254 (2)0.68298 (9)−0.05120 (9)0.0237 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03018 (16)0.01496 (15)0.02675 (16)0.00253 (11)0.01013 (12)0.00130 (11)
O10.0654 (10)0.0207 (7)0.0339 (8)−0.0122 (7)0.0046 (7)0.0038 (6)
O20.0864 (12)0.0321 (8)0.0254 (8)−0.0156 (8)0.0070 (8)0.0014 (6)
O30.0322 (7)0.0228 (7)0.0456 (8)−0.0012 (6)0.0167 (6)−0.0025 (6)
O40.0456 (8)0.0273 (7)0.0299 (7)0.0110 (6)0.0125 (6)−0.0006 (6)
O50.178 (2)0.0368 (10)0.0895 (14)−0.0447 (12)0.0982 (16)−0.0147 (9)
O60.0767 (11)0.0299 (8)0.0470 (9)−0.0207 (8)0.0234 (8)−0.0105 (7)
O70.1403 (18)0.0379 (9)0.0362 (9)−0.0227 (10)0.0359 (10)−0.0152 (7)
O80.0765 (11)0.0419 (9)0.0260 (7)−0.0017 (8)0.0243 (7)0.0016 (6)
O90.0714 (10)0.0359 (8)0.0269 (7)−0.0035 (7)0.0281 (7)−0.0002 (6)
O100.0751 (11)0.0284 (8)0.0404 (8)−0.0017 (7)0.0335 (8)−0.0051 (6)
O110.0391 (7)0.0211 (7)0.0442 (8)0.0020 (6)0.0141 (6)0.0095 (6)
O120.0334 (7)0.0211 (6)0.0359 (7)−0.0047 (5)0.0076 (6)0.0014 (5)
O130.0707 (11)0.0586 (11)0.0343 (9)0.0133 (9)0.0147 (8)0.0069 (8)
O140.142 (9)0.066 (6)0.087 (7)0.003 (6)0.001 (7)−0.007 (5)
N10.0324 (8)0.0173 (7)0.0303 (8)0.0015 (6)0.0108 (7)0.0009 (6)
N20.0356 (8)0.0162 (7)0.0235 (7)0.0000 (6)0.0094 (6)0.0008 (6)
C10.0510 (12)0.0183 (9)0.0312 (10)−0.0001 (8)0.0053 (9)−0.0028 (8)
C20.0529 (12)0.0205 (9)0.0272 (10)0.0028 (8)0.0047 (9)0.0012 (8)
C30.0334 (10)0.0235 (9)0.0282 (10)−0.0008 (8)0.0051 (8)0.0033 (7)
C40.0363 (10)0.0184 (9)0.0313 (10)−0.0048 (7)0.0065 (8)−0.0022 (7)
C50.0310 (9)0.0172 (8)0.0292 (9)0.0023 (7)0.0127 (8)0.0018 (7)
C60.0294 (9)0.0187 (9)0.0270 (9)−0.0001 (7)0.0078 (7)−0.0003 (7)
C70.0573 (12)0.0190 (9)0.0288 (10)0.0031 (8)0.0189 (9)−0.0033 (7)
C80.0582 (12)0.0233 (9)0.0255 (10)0.0008 (9)0.0198 (9)−0.0006 (8)
C90.0421 (10)0.0215 (9)0.0242 (9)0.0005 (8)0.0148 (8)0.0013 (7)
C100.0428 (11)0.0201 (9)0.0268 (9)0.0015 (8)0.0162 (8)−0.0028 (7)
C120.0360 (10)0.0174 (9)0.0263 (9)0.0006 (7)0.0119 (8)0.0035 (7)
C130.0464 (11)0.0254 (10)0.0271 (10)−0.0056 (8)0.0032 (9)−0.0015 (8)
C140.0528 (13)0.0314 (11)0.0254 (10)−0.0017 (9)−0.0021 (9)0.0072 (8)
C150.0443 (11)0.0201 (9)0.0312 (10)−0.0003 (8)0.0091 (9)0.0070 (8)
C160.0340 (9)0.0198 (9)0.0260 (9)0.0000 (7)0.0123 (8)0.0021 (7)
C170.0342 (10)0.0228 (9)0.0217 (9)0.0005 (7)0.0089 (7)0.0030 (7)
C180.0393 (10)0.0227 (9)0.0278 (10)−0.0021 (8)0.0154 (8)0.0013 (7)
C190.0467 (12)0.0244 (10)0.0439 (12)−0.0072 (9)0.0221 (10)−0.0011 (9)
C200.0374 (10)0.0316 (10)0.0240 (9)0.0008 (8)0.0104 (8)−0.0018 (8)
C210.0280 (9)0.0308 (10)0.0239 (9)−0.0018 (7)0.0104 (7)0.0005 (7)
C220.0314 (9)0.0191 (9)0.0260 (9)−0.0012 (7)0.0157 (8)0.0000 (7)
C230.0278 (9)0.0215 (9)0.0267 (9)−0.0029 (7)0.0102 (7)0.0004 (7)
C240.0311 (9)0.0266 (9)0.0240 (9)−0.0022 (7)0.0134 (7)0.0048 (7)
C250.0245 (8)0.0241 (9)0.0203 (8)−0.0009 (7)0.0073 (7)0.0010 (7)
C260.0243 (8)0.0196 (8)0.0232 (8)0.0004 (7)0.0087 (7)0.0018 (7)
C270.0301 (9)0.0227 (9)0.0233 (9)−0.0012 (7)0.0124 (7)0.0045 (7)
C280.0258 (9)0.0234 (9)0.0216 (9)0.0006 (7)0.0077 (7)0.0006 (7)
Geometric parameters (Å, º) top
Zn1—O42.0798 (13)C4—C51.382 (3)
Zn1—O32.1335 (14)C4—H4A0.9300
Zn1—N12.1689 (14)C5—C61.486 (2)
O1—C181.321 (2)C6—C71.382 (3)
O1—H70.88 (3)C6—C91.394 (2)
O2—C181.204 (2)C7—C81.368 (3)
O3—H10.85 (3)C7—H7A0.9300
O3—H20.81 (3)C8—H8A0.9300
O4—H30.84 (3)C9—C101.371 (2)
O4—H40.90 (3)C9—H9A0.9300
O5—C191.195 (2)C10—H10A0.9300
O6—C191.292 (2)C12—C171.377 (2)
O6—H90.867 (17)C12—C131.387 (3)
O7—C201.260 (2)C13—C141.384 (3)
O8—C201.229 (2)C13—H13A0.9300
O9—C211.315 (2)C14—C151.385 (3)
O9—H80.85 (3)C14—H14A0.9300
O10—C211.212 (2)C15—C161.390 (3)
O11—C221.250 (2)C15—H15A0.9300
O12—C221.266 (2)C16—C171.392 (2)
O13—H50.92 (4)C16—C181.496 (2)
O13—H60.87 (4)C17—H17A0.9300
O14—H100.82 (2)C19—C231.525 (2)
O14—H110.82 (2)C20—C281.531 (2)
N1—C31.337 (2)C21—C251.496 (2)
N1—C11.339 (2)C22—C261.508 (2)
N2—C81.348 (2)C23—C241.399 (2)
N2—C101.352 (2)C23—C281.418 (2)
N2—C121.460 (2)C24—C251.384 (2)
C1—C21.382 (3)C24—H24A0.9300
C1—H1A0.9300C25—C261.396 (2)
C2—C51.392 (3)C26—C271.387 (2)
C2—H2A0.9300C27—C281.392 (2)
C3—C41.380 (2)C27—H27A0.9300
C3—H3A0.9300
O4i—Zn1—O4180.0C10—C9—H9A120.0
O4i—Zn1—O3i91.02 (6)C6—C9—H9A120.0
O4—Zn1—O3i88.98 (6)N2—C10—C9120.95 (16)
O4i—Zn1—O388.98 (6)N2—C10—H10A119.5
O4—Zn1—O391.02 (6)C9—C10—H10A119.5
O3i—Zn1—O3180.0C17—C12—C13121.91 (16)
O4i—Zn1—N188.50 (5)C17—C12—N2118.68 (15)
O4—Zn1—N191.50 (5)C13—C12—N2119.41 (16)
O3i—Zn1—N186.58 (5)C14—C13—C12118.60 (17)
O3—Zn1—N193.42 (5)C14—C13—H13A120.7
O4i—Zn1—N1i91.50 (5)C12—C13—H13A120.7
O4—Zn1—N1i88.50 (5)C13—C14—C15120.55 (18)
O3i—Zn1—N1i93.42 (5)C13—C14—H14A119.7
O3—Zn1—N1i86.58 (5)C15—C14—H14A119.7
N1—Zn1—N1i180.00 (8)C14—C15—C16120.09 (17)
C18—O1—H7113.0 (17)C14—C15—H15A120.0
Zn1—O3—H1107.9 (16)C16—C15—H15A120.0
Zn1—O3—H2122.5 (17)C15—C16—C17119.83 (16)
H1—O3—H2104 (2)C15—C16—C18122.93 (16)
Zn1—O4—H3121.7 (17)C17—C16—C18117.23 (16)
Zn1—O4—H4118.2 (15)C12—C17—C16119.02 (16)
H3—O4—H4103 (2)C12—C17—H17A120.5
C19—O6—H9112 (2)C16—C17—H17A120.5
C21—O9—H8110.3 (18)O2—C18—O1122.97 (17)
H5—O13—H6102 (3)O2—C18—C16123.40 (16)
H10—O14—H11104 (10)O1—C18—C16113.63 (16)
C3—N1—C1116.98 (15)O5—C19—O6120.08 (19)
C3—N1—Zn1120.43 (12)O5—C19—C23119.00 (18)
C1—N1—Zn1122.58 (12)O6—C19—C23120.91 (17)
C8—N2—C10119.85 (15)O8—C20—O7123.68 (18)
C8—N2—C12120.28 (14)O8—C20—C28117.35 (16)
C10—N2—C12119.85 (14)O7—C20—C28118.95 (16)
N1—C1—C2123.42 (17)O10—C21—O9123.79 (17)
N1—C1—H1A118.3O10—C21—C25121.67 (16)
C2—C1—H1A118.3O9—C21—C25114.51 (16)
C1—C2—C5119.20 (17)O11—C22—O12125.74 (16)
C1—C2—H2A120.4O11—C22—C26118.48 (15)
C5—C2—H2A120.4O12—C22—C26115.63 (15)
N1—C3—C4123.26 (17)C24—C23—C28118.29 (15)
N1—C3—H3A118.4C24—C23—C19112.65 (15)
C4—C3—H3A118.4C28—C23—C19129.02 (16)
C3—C4—C5119.72 (17)C25—C24—C23122.71 (15)
C3—C4—H4A120.1C25—C24—H24A118.6
C5—C4—H4A120.1C23—C24—H24A118.6
C4—C5—C2117.37 (16)C24—C25—C26118.93 (15)
C4—C5—C6120.26 (16)C24—C25—C21121.64 (15)
C2—C5—C6122.36 (16)C26—C25—C21119.03 (15)
C7—C6—C9117.70 (16)C27—C26—C25118.78 (15)
C7—C6—C5121.10 (15)C27—C26—C22117.73 (15)
C9—C6—C5121.18 (16)C25—C26—C22123.32 (15)
C8—C7—C6120.62 (17)C26—C27—C28123.08 (15)
C8—C7—H7A119.7C26—C27—H27A118.5
C6—C7—H7A119.7C28—C27—H27A118.5
N2—C8—C7120.86 (17)C27—C28—C23117.96 (15)
N2—C8—H8A119.6C27—C28—C20113.79 (15)
C7—C8—H8A119.6C23—C28—C20128.25 (16)
C10—C9—C6119.99 (16)
Symmetry code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H7···O12ii0.87 (2)1.80 (3)2.656 (3)164 (3)
O3—H1···O11iii0.85 (2)1.88 (3)2.732 (2)175 (3)
O3—H2···O11iv0.81 (3)2.03 (2)2.820 (4)163 (2)
O4—H3···O13iv0.84 (2)1.84 (3)2.677 (6)175 (3)
O4—H4···O12v0.90 (3)1.79 (4)2.694 (2)177 (4)
O6—H9···O70.87 (3)1.56 (3)2.418 (2)174 (3)
O9—H8···O8iv0.85 (3)1.82 (3)2.646 (3)163 (4)
O13—H5···O100.92 (4)1.90 (2)2.813 (3)174 (3)
O13—H6···O7iv0.87 (4)1.86 (4)2.723 (2)169 (3)
O14—H11···O130.82 (2)2.18 (2)2.846 (2)138 (2)
C7—H7A···O1vi0.932.303.155 (2)153
C8—H8A···O12vii0.932.523.302 (2)142
C9—H9A···O2viii0.932.303.225 (2)172
C10—H10A···O5ix0.932.153.060 (3)167
Symmetry codes: (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) x, −y+3/2, z+1/2; (v) x−1, −y+3/2, z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) x−1, y, z; (viii) −x+1, −y+2, −z+1; (ix) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[Zn(C17H13N2O2)2(H2O)4](C10H4O8)2·2.5H2O
Mr1241.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)7.5476 (2), 19.5528 (4), 19.2752 (4)
β (°) 110.431 (2)
V (Å3)2665.63 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.56
Crystal size (mm)0.43 × 0.41 × 0.37
Data collection
DiffractometerBruker APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.781, 0.825
No. of measured, independent and
observed [I > 2σ(I)] reflections		25451, 4867, 4250
Rint0.028
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.078, 1.06
No. of reflections4867
No. of parameters429
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.29, −0.36

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H7···O12i0.87 (2)1.80 (3)2.656 (3)164 (3)
O3—H1···O11ii0.85 (2)1.88 (3)2.732 (2)175 (3)
O3—H2···O11iii0.81 (3)2.03 (2)2.820 (4)163 (2)
O4—H3···O13iii0.84 (2)1.84 (3)2.677 (6)175 (3)
O4—H4···O12iv0.90 (3)1.79 (4)2.694 (2)177 (4)
O6—H9···O70.87 (3)1.56 (3)2.418 (2)174 (3)
O9—H8···O8iii0.85 (3)1.82 (3)2.646 (3)163 (4)
O13—H5···O100.92 (4)1.90 (2)2.813 (3)174 (3)
O13—H6···O7iii0.87 (4)1.86 (4)2.723 (2)169 (3)
O14—H11···O130.82 (2)2.18 (2)2.846 (2)138 (2)
C7—H7A···O1v0.932.303.155 (2)153
C8—H8A···O12vi0.932.523.302 (2)142
C9—H9A···O2vii0.932.303.225 (2)172
C10—H10A···O5viii0.932.153.060 (3)167
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x−1, −y+3/2, z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) x−1, y, z; (vii) −x+1, −y+2, −z+1; (viii) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

The authors thank the NNSFC (grant Nos. 21053001 and 20701014), the Fundamental Research Funds for the Central Universities (2009ZM0030) and the SRP program of the SCUT for financial support. They also thank Professor Tong Chun Kuang (Analytical and Testing Center of SCUT) for the data collection.

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationEbbesen, T. W., Manring, L. E. & Peters, K. S. (1984). J. Am. Chem. Soc. 106, 7400–7404.  CrossRef CAS Web of Science Google Scholar
 First citationJin, X.-H., Sun, J.-K., Xu, X.-M., Li, Z.-H. & Zhang, J. (2010). Chem. Commun. 46, 4695–4697.  Web of Science CSD 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 citationSun, Y.-Q., Zhang, J., Ju, Z.-F. & Yang, G.-Y. (2005). Cryst. Growth Des. 5, 1939–1943.  Web of Science CSD CrossRef CAS Google Scholar
 First citationXu, G., Guo, G.-C., Wang, M.-S. & Zhang, Z.-G. (2007). Angew. Chem. Int. Ed. 46, 3249–3251.  Web of Science CSD CrossRef CAS Google Scholar

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1701-m1702
https://doi.org/10.1107/S1600536811045156
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