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A new three-dimensional metal–organic framework, {[Zn2(C16H6O9)(C10H8N2)(H2O)]·0.5C10H8N2}n, is a porous three-dimensional bipyridyl-pillared framework with rhombic channels built from two-dimensional helical double layers of Zn–DETA [DETA is 4,4′-oxydi(benzene-1,2- carboxyl­ate)] with the 4,4′-bipyridyl guest mol­ecules locked in the cavities through short O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016893/gg3085sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016893/gg3085Isup2.hkl
Contains datablock I

CCDC reference: 660044

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.048
  • wR factor = 0.099
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C29 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The rational design and synthesis of extended metal-organic frameworks (MOFs) is important and amongst the new classes of solid functional materials has applications in magnetism, as optical materials, in catalysis and gas absorption/separation, but also by their novel diverse molecular architectures and topologies (Zheng et al., 2006; Sun et al., 2006; Fujita et al., 1994; Dietzel et al., 2006). In this family, metal carboxylates have attracted much attention: among the numerous ligands employed in this field, by far the most common are the rigid aromatic polycarboxylate ligands including 1,2-benzenedicarboxylate, 1,3,5-benzenetricarboxylate and 1,2,4,5-benzenetetracarboxylate, which have been extensively utilized in the fabrication of extended MOFs with interesting structures and desired properties (Cheng et al., 2006; Chui et al., 1999; Li et al., 1999). However, reports on MOFs based on flexible polycarboxylate ligands have been relatively scarce. Against this background, we have selected a flexible divergent carboxylic acid 3,3',4,4'-diphenyl ether-tetracarboxylic acid (H4DETA), to construct new complexes with the cooperativity of an auxiliary bpy ligand as a rigid organic spacer. The title compound, (I), was obtained under hydrothermal conditions as a pale yellow solid in good yield.

There are two crystallographically independent Zn centers in the asymmetric unit (Fig. 1). The Zn1 center has a distorted tetrahedral coordination geometry being defined by three carboxylate atoms from three different DETA ligands with Zn—O distances from 1.942 (3) to 1.975 (3) Å, and a N atom (Zn1—N = 2.045 (3) Å) from a bpy ligand occupying the 4t h site, whereas the Zn2 center is coordinated by four carboxylate atoms from two distinct DETA ligands Zn—O 2.008 (3) to 2.099 (3) Å, a longer Zn—O 2.373 (4) Å, Zn—Oaqua 2.180 (3) Å and one bipy N atom Zn—N at 2.086 (4) Å, providing a highly distorted octahedral coordination polyhedron (with two O sites at symmetry related positions). The Zn—O and Zn—N distances at Zn2 are slightly longer than those at Zn1 but all values are comparable with those reported for Zn related complexes (Tao et al., 2000; Wang et al., 2006; He et al., 2006; Hong 2005). There is also a unique DETA ligand in the fundamental unit of (I), which is bent about the central ether bond with a dihedral angle between the two phenyl rings of 72.28 (2)°. The V-shaped DETA favors the formation of helices as authenticated by BTDC (where BTDC is 3,3',4,4'-benzophenone tetracarboxylate). (Hong 2005; Xiao et al., 2006). It serves as a tetra-connector with its four carboxylate arms in three coordination modes, monodentate, bidentate and syn—anti bridging bidentate, linking Zn atoms into 2-D (two-dimensional) helical double layer subunit, (Fig. 2). There are no Zn···Zn interactions.

A feature of (I) is the two-dimensional helical double layers which are further pillared up by bpy ligands resulting in a 3-D host–guest structure: the neutral 3-D host architecture of Zn—DETA—bpy, which consists of one-dimensional rhombus channels along the [100] direction (Fig. 3), encapsulates the guest bpy ligands via hydrogen bonding interactions between the guest bpy ligands and the nearest coordinated water molecules (O1W—H1W···N3, 2.859 (6) Å).

Related literature top

For related literature, see: Cheng et al. (2006); Chui et al. (1999); Dietzel et al. (2006); Fujita et al. (1994); He et al. (2006); Hong (2005); Li et al. (1999); Sun et al. (2006); Wang et al. (2006); Xiao et al. (2006); Zheng et al. (2006).

Experimental top

A mixture of Zn(CH3CO2)2.2H2O (0.120 g, 0.55 mmol), 4,4'-oxyphthalic anhydride (0.081 g, 0.26 mmol), 4,4'-bpy (0.088 g, 0.56 mmol) in a molar ratio of about 2.1:1:2.1 and water (15 ml) were placed in a 25 ml Teflon-lined stainless steel reactor and heated to 453 K for 76 h. When the reactor was cooled to room temperature over a period of 3 d, yellow prismatic single crystals suitable for X-ray diffraction were obtained.

Refinement top

All H atoms, except for the aqua H atoms, were positioned geometrically and refined using a riding model [C—H = 0.93 Å] and Uiso(H) = 1.2Ueq(C). The water H atoms were located from difference maps and refined isotropically, with O—H distances fixed at 0.82/0.85 Å and with Uiso(H) = 1.5Ueq(O).

Structure description top

The rational design and synthesis of extended metal-organic frameworks (MOFs) is important and amongst the new classes of solid functional materials has applications in magnetism, as optical materials, in catalysis and gas absorption/separation, but also by their novel diverse molecular architectures and topologies (Zheng et al., 2006; Sun et al., 2006; Fujita et al., 1994; Dietzel et al., 2006). In this family, metal carboxylates have attracted much attention: among the numerous ligands employed in this field, by far the most common are the rigid aromatic polycarboxylate ligands including 1,2-benzenedicarboxylate, 1,3,5-benzenetricarboxylate and 1,2,4,5-benzenetetracarboxylate, which have been extensively utilized in the fabrication of extended MOFs with interesting structures and desired properties (Cheng et al., 2006; Chui et al., 1999; Li et al., 1999). However, reports on MOFs based on flexible polycarboxylate ligands have been relatively scarce. Against this background, we have selected a flexible divergent carboxylic acid 3,3',4,4'-diphenyl ether-tetracarboxylic acid (H4DETA), to construct new complexes with the cooperativity of an auxiliary bpy ligand as a rigid organic spacer. The title compound, (I), was obtained under hydrothermal conditions as a pale yellow solid in good yield.

There are two crystallographically independent Zn centers in the asymmetric unit (Fig. 1). The Zn1 center has a distorted tetrahedral coordination geometry being defined by three carboxylate atoms from three different DETA ligands with Zn—O distances from 1.942 (3) to 1.975 (3) Å, and a N atom (Zn1—N = 2.045 (3) Å) from a bpy ligand occupying the 4t h site, whereas the Zn2 center is coordinated by four carboxylate atoms from two distinct DETA ligands Zn—O 2.008 (3) to 2.099 (3) Å, a longer Zn—O 2.373 (4) Å, Zn—Oaqua 2.180 (3) Å and one bipy N atom Zn—N at 2.086 (4) Å, providing a highly distorted octahedral coordination polyhedron (with two O sites at symmetry related positions). The Zn—O and Zn—N distances at Zn2 are slightly longer than those at Zn1 but all values are comparable with those reported for Zn related complexes (Tao et al., 2000; Wang et al., 2006; He et al., 2006; Hong 2005). There is also a unique DETA ligand in the fundamental unit of (I), which is bent about the central ether bond with a dihedral angle between the two phenyl rings of 72.28 (2)°. The V-shaped DETA favors the formation of helices as authenticated by BTDC (where BTDC is 3,3',4,4'-benzophenone tetracarboxylate). (Hong 2005; Xiao et al., 2006). It serves as a tetra-connector with its four carboxylate arms in three coordination modes, monodentate, bidentate and syn—anti bridging bidentate, linking Zn atoms into 2-D (two-dimensional) helical double layer subunit, (Fig. 2). There are no Zn···Zn interactions.

A feature of (I) is the two-dimensional helical double layers which are further pillared up by bpy ligands resulting in a 3-D host–guest structure: the neutral 3-D host architecture of Zn—DETA—bpy, which consists of one-dimensional rhombus channels along the [100] direction (Fig. 3), encapsulates the guest bpy ligands via hydrogen bonding interactions between the guest bpy ligands and the nearest coordinated water molecules (O1W—H1W···N3, 2.859 (6) Å).

For related literature, see: Cheng et al. (2006); Chui et al. (1999); Dietzel et al. (2006); Fujita et al. (1994); He et al. (2006); Hong (2005); Li et al. (1999); Sun et al. (2006); Wang et al. (2006); Xiao et al. (2006); Zheng et al. (2006).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1996); data reduction: XPREP (Siemens, 1996); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. ORTEP representation of the coordination environment around the Zn centers, showing the atom-numbering scheme. Displacement ellipsoids are plotted at the 50% probability level. H atoms have been omitted for clarity [Symmetry codes: (a) -x, 1 - y, -z; (b) 1/2 - x, 1/2 + y, 1/2 - z; (c) 1/2 - x, -1/2 + y, -1/2 - z; (d) -x, 1 - y, -z; e, -x, 1 - y, -1 - z].
[Figure 2] Fig. 2. View of the two-dimensional helical double layer in (I).
[Figure 3] Fig. 3. Perspective view of the 3-D framework, highlighting the 1-D rhombus channels. Guest bpy molecules included in the channels are omitted for clarity.
Poly[[aqua(µ2-4,4'-bipyridine)(µ4-4,4'-oxydibenzene-1,2- carboxylato)dizinc(II)] 4,4'-bipyridine hemisolvate] top
Crystal data top
[Zn2(C16H6O9)(C10H8N2)(H2O)]·0.5C10H8N2F(000) = 1468
Mr = 725.28Dx = 1.759 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4772 reflections
a = 10.9516 (4) Åθ = 1.8–25.7°
b = 15.1202 (5) ŵ = 1.82 mm1
c = 16.5498 (4) ÅT = 293 K
β = 92.063 (1)°Prism, yellow
V = 2738.71 (15) Å30.28 × 0.25 × 0.20 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
5211 independent reflections
Radiation source: fine-focus sealed tube3672 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 25.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.606, Tmax = 0.695k = 1818
13598 measured reflectionsl = 2011
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0268P)2 + 5.3897P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
5211 reflectionsΔρmax = 0.50 e Å3
415 parametersΔρmin = 0.63 e Å3
2 restraints
Crystal data top
[Zn2(C16H6O9)(C10H8N2)(H2O)]·0.5C10H8N2V = 2738.71 (15) Å3
Mr = 725.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.9516 (4) ŵ = 1.82 mm1
b = 15.1202 (5) ÅT = 293 K
c = 16.5498 (4) Å0.28 × 0.25 × 0.20 mm
β = 92.063 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
5211 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3672 reflections with I > 2σ(I)
Tmin = 0.606, Tmax = 0.695Rint = 0.054
13598 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048415 parameters
wR(F2) = 0.0992 restraints
S = 1.08Δρmax = 0.50 e Å3
5211 reflectionsΔρmin = 0.63 e Å3
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
Zn10.28659 (5)0.39722 (3)0.03206 (3)0.02325 (14)
Zn20.10394 (5)0.35096 (3)0.13285 (3)0.02633 (15)
O1W0.2490 (3)0.3177 (2)0.22115 (19)0.0378 (8)
H1WA0.22980.27330.24620.057*
H1WB0.26480.35510.25830.057*
O10.0277 (3)0.3752 (2)0.04076 (17)0.0335 (8)
O20.1330 (3)0.3517 (2)0.07326 (18)0.0320 (7)
O30.2645 (3)0.49931 (19)0.03977 (18)0.0319 (8)
O40.2214 (3)0.4210 (2)0.06792 (18)0.0374 (8)
O50.0825 (3)0.0796 (2)0.38851 (18)0.0323 (8)
O60.1656 (3)0.1681 (2)0.29850 (19)0.0379 (8)
O70.0057 (3)0.2528 (2)0.1830 (2)0.0473 (10)
O80.1323 (4)0.1990 (3)0.1029 (2)0.0599 (11)
O90.1372 (3)0.1490 (2)0.22898 (18)0.0388 (8)
N10.0411 (3)0.4590 (2)0.1978 (2)0.0270 (9)
N20.1499 (3)0.8058 (2)0.4527 (2)0.0266 (9)
N30.2168 (5)0.3922 (4)0.3780 (3)0.0637 (14)
C10.1547 (4)0.2161 (3)0.1711 (3)0.0311 (11)
C20.0578 (4)0.2483 (3)0.1292 (3)0.0291 (11)
H2B0.01970.22420.13770.035*
C30.0761 (4)0.3176 (3)0.0734 (2)0.0216 (9)
C40.1928 (4)0.3543 (3)0.0637 (2)0.0223 (9)
C50.2867 (4)0.3236 (3)0.1104 (3)0.0299 (11)
H50.36270.35100.10620.036*
C60.2696 (4)0.2530 (3)0.1631 (3)0.0326 (11)
H60.33400.23110.19230.039*
C70.0348 (4)0.3511 (3)0.0313 (3)0.0235 (10)
C80.2258 (4)0.4302 (3)0.0075 (3)0.0225 (10)
C90.0858 (4)0.0700 (3)0.2056 (3)0.0280 (11)
C100.0280 (4)0.0212 (3)0.2669 (3)0.0296 (11)
H100.02100.04440.31890.036*
C110.0193 (4)0.0620 (3)0.2513 (3)0.0236 (10)
C120.0088 (4)0.0963 (3)0.1728 (3)0.0273 (10)
C130.0484 (5)0.0449 (3)0.1119 (3)0.0357 (12)
H130.05540.06730.05960.043*
C140.0945 (4)0.0380 (3)0.1275 (3)0.0345 (12)
H140.13090.07160.08620.041*
C150.0944 (4)0.1088 (3)0.3168 (3)0.0263 (10)
C160.0501 (5)0.1880 (3)0.1511 (3)0.0389 (13)
C170.0756 (4)0.4700 (3)0.2140 (3)0.0367 (12)
H170.13260.42940.19350.044*
C180.1155 (5)0.5394 (3)0.2603 (3)0.0410 (13)
H180.19830.54510.26980.049*
C190.0339 (4)0.6006 (3)0.2929 (2)0.0241 (10)
C200.0867 (4)0.5901 (3)0.2732 (3)0.0361 (12)
H200.14530.63060.29150.043*
C210.1202 (5)0.5192 (3)0.2263 (3)0.0354 (12)
H210.20190.51330.21390.042*
C220.2286 (5)0.7506 (3)0.4162 (3)0.0451 (14)
H220.31120.75630.42650.054*
C230.1937 (5)0.6853 (3)0.3639 (3)0.0460 (14)
H230.25270.64880.33970.055*
C240.0727 (4)0.6734 (3)0.3469 (3)0.0268 (10)
C250.0089 (4)0.7326 (3)0.3832 (3)0.0374 (12)
H250.09180.72870.37310.045*
C260.0329 (4)0.7973 (3)0.4344 (3)0.0358 (12)
H260.02350.83690.45730.043*
C270.2418 (6)0.4675 (5)0.4165 (4)0.073 (2)
H270.31860.49230.41070.088*
C280.1606 (6)0.5114 (4)0.4650 (4)0.0627 (18)
H280.18360.56400.49040.075*
C290.0460 (5)0.4770 (4)0.4753 (3)0.0437 (14)
C300.0191 (6)0.3989 (4)0.4357 (4)0.0646 (18)
H300.05730.37280.44030.077*
C310.1056 (7)0.3594 (4)0.3892 (4)0.074 (2)
H310.08520.30620.36400.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0235 (3)0.0229 (3)0.0233 (3)0.0029 (2)0.0008 (2)0.0003 (2)
Zn20.0308 (3)0.0257 (3)0.0228 (3)0.0013 (2)0.0042 (2)0.0018 (2)
O1W0.035 (2)0.0387 (19)0.040 (2)0.0004 (15)0.0028 (16)0.0032 (16)
O10.0298 (19)0.051 (2)0.0194 (17)0.0076 (15)0.0007 (14)0.0065 (14)
O20.0225 (18)0.0423 (19)0.0310 (17)0.0011 (15)0.0006 (14)0.0051 (15)
O30.044 (2)0.0240 (17)0.0278 (17)0.0096 (15)0.0028 (15)0.0020 (14)
O40.046 (2)0.046 (2)0.0207 (17)0.0228 (17)0.0052 (15)0.0053 (15)
O50.0323 (19)0.0406 (19)0.0237 (17)0.0031 (15)0.0011 (14)0.0015 (14)
O60.037 (2)0.0361 (19)0.040 (2)0.0130 (16)0.0106 (16)0.0065 (15)
O70.045 (2)0.0231 (18)0.073 (3)0.0018 (16)0.020 (2)0.0029 (18)
O80.075 (3)0.060 (3)0.046 (2)0.022 (2)0.012 (2)0.007 (2)
O90.057 (2)0.0313 (18)0.0287 (18)0.0116 (17)0.0087 (16)0.0111 (15)
N10.033 (2)0.025 (2)0.023 (2)0.0009 (17)0.0020 (17)0.0011 (16)
N20.026 (2)0.026 (2)0.029 (2)0.0028 (17)0.0012 (17)0.0047 (17)
N30.070 (4)0.071 (4)0.051 (3)0.008 (3)0.010 (3)0.000 (3)
C10.038 (3)0.025 (2)0.030 (3)0.001 (2)0.007 (2)0.007 (2)
C20.025 (3)0.025 (2)0.037 (3)0.007 (2)0.002 (2)0.004 (2)
C30.025 (3)0.023 (2)0.018 (2)0.0019 (19)0.0005 (18)0.0011 (18)
C40.023 (2)0.019 (2)0.025 (2)0.0032 (19)0.0013 (18)0.0013 (19)
C50.021 (3)0.031 (3)0.038 (3)0.009 (2)0.007 (2)0.006 (2)
C60.025 (3)0.032 (3)0.041 (3)0.000 (2)0.009 (2)0.007 (2)
C70.022 (2)0.021 (2)0.027 (3)0.0039 (19)0.002 (2)0.001 (2)
C80.012 (2)0.026 (2)0.029 (3)0.0018 (18)0.0020 (19)0.0027 (19)
C90.026 (3)0.017 (2)0.041 (3)0.0009 (19)0.005 (2)0.005 (2)
C100.034 (3)0.024 (2)0.031 (3)0.002 (2)0.003 (2)0.001 (2)
C110.023 (2)0.020 (2)0.027 (2)0.0007 (19)0.0024 (19)0.0027 (19)
C120.025 (3)0.020 (2)0.037 (3)0.0017 (19)0.002 (2)0.002 (2)
C130.044 (3)0.032 (3)0.030 (3)0.001 (2)0.006 (2)0.000 (2)
C140.040 (3)0.026 (3)0.037 (3)0.001 (2)0.004 (2)0.007 (2)
C150.021 (2)0.025 (2)0.033 (3)0.007 (2)0.001 (2)0.002 (2)
C160.046 (3)0.037 (3)0.033 (3)0.009 (3)0.020 (3)0.007 (2)
C170.026 (3)0.038 (3)0.046 (3)0.006 (2)0.001 (2)0.019 (2)
C180.026 (3)0.044 (3)0.053 (3)0.002 (2)0.001 (2)0.020 (3)
C190.025 (3)0.024 (2)0.023 (2)0.001 (2)0.0007 (19)0.0003 (19)
C200.032 (3)0.027 (3)0.050 (3)0.006 (2)0.014 (2)0.013 (2)
C210.030 (3)0.033 (3)0.044 (3)0.008 (2)0.012 (2)0.008 (2)
C220.022 (3)0.049 (3)0.065 (4)0.002 (2)0.006 (3)0.028 (3)
C230.033 (3)0.046 (3)0.058 (4)0.007 (3)0.004 (3)0.029 (3)
C240.032 (3)0.022 (2)0.026 (2)0.001 (2)0.002 (2)0.0018 (19)
C250.026 (3)0.042 (3)0.045 (3)0.001 (2)0.009 (2)0.015 (2)
C260.030 (3)0.034 (3)0.043 (3)0.008 (2)0.005 (2)0.012 (2)
C270.048 (4)0.101 (6)0.071 (5)0.001 (4)0.002 (4)0.015 (4)
C280.053 (4)0.079 (5)0.055 (4)0.003 (4)0.013 (3)0.022 (3)
C290.055 (4)0.050 (3)0.025 (3)0.002 (3)0.004 (2)0.007 (2)
C300.082 (5)0.050 (4)0.064 (4)0.012 (3)0.024 (4)0.008 (3)
C310.111 (6)0.049 (4)0.065 (4)0.005 (4)0.035 (4)0.002 (3)
Geometric parameters (Å, º) top
Zn1—O21.962 (3)C5—C61.388 (6)
Zn1—O3i1.975 (3)C5—H50.9300
Zn1—O5ii1.942 (3)C6—H60.9300
Zn1—N2iii2.045 (3)C9—C141.380 (6)
Zn2—N12.086 (3)C9—C101.388 (6)
Zn2—O12.092 (3)C10—C111.389 (6)
Zn2—O42.008 (3)C10—H100.9300
Zn2—O7iv2.099 (3)C11—C121.399 (6)
Zn2—O8iv2.373 (4)C11—C151.513 (6)
Zn2—O1W2.179 (3)C12—C131.402 (6)
Zn2—C16iv2.554 (5)C12—C161.506 (6)
O1W—H1WA0.8200C13—C141.379 (6)
O1W—H1WB0.8486C13—H130.9300
O1—C71.246 (5)C14—H140.9300
O2—C71.260 (5)C16—Zn2iv2.554 (5)
O3—C81.254 (5)C17—C181.380 (6)
O3—Zn1i1.975 (3)C17—H170.9300
O4—C81.258 (5)C18—C191.383 (6)
O5—C151.278 (5)C18—H180.9300
O5—Zn1v1.942 (3)C19—C201.381 (6)
O6—C151.233 (5)C19—C241.489 (6)
O7—C161.278 (6)C20—C211.381 (6)
O7—Zn2iv2.099 (3)C20—H200.9300
O8—C161.235 (6)C21—H210.9300
O8—Zn2iv2.373 (4)C22—C231.376 (6)
O9—C91.381 (5)C22—H220.9300
O9—C11.404 (5)C23—C241.377 (6)
N1—C171.326 (6)C23—H230.9300
N1—C211.331 (6)C24—C251.387 (6)
N2—C221.330 (6)C25—C261.384 (6)
N2—C261.334 (6)C25—H250.9300
N2—Zn1vi2.045 (3)C26—H260.9300
N3—C271.328 (8)C27—C281.388 (8)
N3—C311.334 (8)C27—H270.9300
C1—C61.378 (6)C28—C291.375 (8)
C1—C21.378 (6)C28—H280.9300
C2—C31.405 (6)C29—C301.379 (7)
C2—H2B0.9300C29—C29vii1.491 (11)
C3—C41.398 (6)C30—C311.377 (8)
C3—C71.509 (6)C30—H300.9300
C4—C51.388 (6)C31—H310.9300
C4—C81.513 (6)
O5ii—Zn1—O2116.70 (13)O9—C9—C10115.8 (4)
O5ii—Zn1—O3i109.63 (13)C9—C10—C11120.6 (4)
O2—Zn1—O3i113.51 (13)C9—C10—H10119.7
O5ii—Zn1—N2iii107.27 (14)C11—C10—H10119.7
O2—Zn1—N2iii107.57 (14)C10—C11—C12119.3 (4)
O3i—Zn1—N2iii100.73 (13)C10—C11—C15119.2 (4)
O4—Zn2—N195.29 (14)C12—C11—C15121.1 (4)
O4—Zn2—O187.45 (13)C11—C12—C13118.8 (4)
N1—Zn2—O190.38 (13)C11—C12—C16123.1 (4)
O4—Zn2—O7iv166.27 (14)C13—C12—C16118.0 (4)
N1—Zn2—O7iv98.40 (14)C14—C13—C12121.7 (4)
O1—Zn2—O7iv91.34 (13)C14—C13—H13119.1
O4—Zn2—O1W90.86 (13)C12—C13—H13119.1
N1—Zn2—O1W94.67 (13)C13—C14—C9118.7 (4)
O1—Zn2—O1W174.81 (12)C13—C14—H14120.6
O7iv—Zn2—O1W89.13 (12)C9—C14—H14120.6
O4—Zn2—O8iv107.94 (14)O6—C15—O5124.5 (4)
N1—Zn2—O8iv156.04 (14)O6—C15—C11119.7 (4)
O1—Zn2—O8iv96.31 (13)O5—C15—C11115.6 (4)
O7iv—Zn2—O8iv58.59 (14)O8—C16—O7122.3 (5)
O1W—Zn2—O8iv79.54 (13)O8—C16—C12120.6 (5)
O4—Zn2—C16iv136.67 (17)O7—C16—C12117.1 (5)
N1—Zn2—C16iv127.79 (17)O8—C16—Zn2iv67.5 (3)
O1—Zn2—C16iv95.69 (14)O7—C16—Zn2iv54.9 (2)
O7iv—Zn2—C16iv29.90 (16)C12—C16—Zn2iv171.5 (4)
O1W—Zn2—C16iv82.18 (13)N1—C17—C18122.3 (4)
O8iv—Zn2—C16iv28.74 (15)N1—C17—H17118.9
Zn2—O1W—H1WA109.5C18—C17—H17118.9
Zn2—O1W—H1WB117.2C17—C18—C19120.9 (5)
H1WA—O1W—H1WB103.2C17—C18—H18119.6
C7—O1—Zn2131.5 (3)C19—C18—H18119.6
C7—O2—Zn1122.5 (3)C20—C19—C18116.1 (4)
C8—O3—Zn1i116.1 (3)C20—C19—C24121.6 (4)
C8—O4—Zn2129.6 (3)C18—C19—C24122.3 (4)
C15—O5—Zn1v117.9 (3)C21—C20—C19119.9 (4)
C16—O7—Zn2iv95.2 (3)C21—C20—H20120.1
C16—O8—Zn2iv83.8 (3)C19—C20—H20120.1
C9—O9—C1118.8 (3)N1—C21—C20123.2 (4)
C17—N1—C21117.5 (4)N1—C21—H21118.4
C17—N1—Zn2122.7 (3)C20—C21—H21118.4
C21—N1—Zn2119.7 (3)N2—C22—C23123.1 (5)
C22—N2—C26116.7 (4)N2—C22—H22118.4
C22—N2—Zn1vi119.1 (3)C23—C22—H22118.4
C26—N2—Zn1vi124.3 (3)C22—C23—C24120.9 (5)
C27—N3—C31115.1 (6)C22—C23—H23119.5
C6—C1—C2121.7 (4)C24—C23—H23119.5
C6—C1—O9117.4 (4)C23—C24—C25116.0 (4)
C2—C1—O9120.7 (4)C23—C24—C19121.2 (4)
C1—C2—C3120.0 (4)C25—C24—C19122.9 (4)
C1—C2—H2B120.0C26—C25—C24120.0 (4)
C3—C2—H2B120.0C26—C25—H25120.0
C4—C3—C2118.6 (4)C24—C25—H25120.0
C4—C3—C7124.1 (4)N2—C26—C25123.3 (4)
C2—C3—C7117.1 (4)N2—C26—H26118.3
C5—C4—C3119.8 (4)C25—C26—H26118.3
C5—C4—C8115.4 (4)N3—C27—C28124.2 (7)
C3—C4—C8124.7 (4)N3—C27—H27117.9
C6—C5—C4121.4 (4)C28—C27—H27117.9
C6—C5—H5119.3C29—C28—C27119.8 (6)
C4—C5—H5119.3C29—C28—H28120.1
C1—C6—C5118.3 (4)C27—C28—H28120.1
C1—C6—H6120.8C28—C29—C30116.4 (5)
C5—C6—H6120.8C28—C29—C29vii122.0 (7)
O1—C7—O2123.2 (4)C30—C29—C29vii121.6 (7)
O1—C7—C3121.1 (4)C31—C30—C29119.8 (6)
O2—C7—C3115.6 (4)C31—C30—H30120.1
O3—C8—O4122.7 (4)C29—C30—H30120.1
O3—C8—C4116.6 (4)N3—C31—C30124.5 (6)
O4—C8—C4120.6 (4)N3—C31—H31117.7
C14—C9—O9123.4 (4)C30—C31—H31117.7
C14—C9—C10120.8 (4)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z1/2; (iv) x, y, z; (v) x+1/2, y1/2, z+1/2; (vi) x+1/2, y+1/2, z1/2; (vii) x, y+1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O6iv0.821.952.770 (4)173
O1W—H1WB···N30.852.142.863 (6)143
Symmetry code: (iv) x, y, z.

Experimental details

Crystal data
Chemical formula[Zn2(C16H6O9)(C10H8N2)(H2O)]·0.5C10H8N2
Mr725.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)10.9516 (4), 15.1202 (5), 16.5498 (4)
β (°) 92.063 (1)
V3)2738.71 (15)
Z4
Radiation typeMo Kα
µ (mm1)1.82
Crystal size (mm)0.28 × 0.25 × 0.20
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.606, 0.695
No. of measured, independent and
observed [I > 2σ(I)] reflections
13598, 5211, 3672
Rint0.054
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.099, 1.08
No. of reflections5211
No. of parameters415
No. of restraints2
Δρmax, Δρmin (e Å3)0.50, 0.63

Computer programs: SMART (Siemens, 1996), SMART and SAINT (Siemens, 1996), XPREP (Siemens, 1996), SHELXTL (Bruker, 1997), SHELXTL.

Selected bond lengths (Å) top
Zn1—O21.962 (3)Zn2—O12.092 (3)
Zn1—O3i1.975 (3)Zn2—O42.008 (3)
Zn1—O5ii1.942 (3)Zn2—O7iv2.099 (3)
Zn1—N2iii2.045 (3)Zn2—O8iv2.373 (4)
Zn2—N12.086 (3)Zn2—O1W2.179 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z1/2; (iv) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O6iv0.821.952.770 (4)173
O1W—H1WB···N30.852.142.863 (6)143
Symmetry code: (iv) x, y, z.
 

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