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A metal–organic framework with a novel topology, poly[sesqui(μ2-4,4′-bi­pyridine)­bis­(di­methyl­formamide)­bis­(μ4-4,4′,4′′-nitrilo­tribenzoato)trizinc(II)], [Zn3(C21H12NO6)2(C10H8N2)1.5(C3H7NO)2]n, was obtained by the solvothermal method using 4,4′,4′′-nitrilo­tri­benzoic acid and 4,4′-bi­pyridine (bipy). The structure, determined by single-crystal X-ray diffraction analysis, possesses three kinds of crystallographically independent ZnII cations, as well as binuclear Zn2(COO)4(bipy)2 paddle-wheel clusters, and can be reduced to a novel topology of a (3,3,6)-connected 3-nodal net, with the Schläfli symbol {5.62}4{52.6}4{58.87} according to the topological analysis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615014813/yo3010sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615014813/yo3010Isup2.hkl
Contains datablock I

CCDC reference: 1417420

Introduction top

Nowadays, the study of metal–organic frameworks (MOFs) is one of the most fascinating fields in materials science and inorganic chemistry because of the versatility of their structures and varieties of their functions, such as catalysis (Yoon et al., 2011), gas adsorption (Suh et al., 2012), electrical conductivity (Talin et al., 2014), luminescence (Cui et al., 2012; Yang et al., 2011) and nonlinear optical materials (Wang et al., 2012). MOFs are usually self-assembled from metal ions and organic ligands, and it is obvious that the organic ligands play a vital role in the design and synthesis of functional MOFs. Such ligands include N- or O-coordinated single ligands and other sufficiently attractive multiple ligands (Robin & Fromm, 2006; Paul et al., 2014; Lee et al., 2011).

Aromatic polycarboxyl­ate ligands, such as 4,4',4''-nitrilo­tri­benzoic acid (H3TCA), have been used widely in the construction of inter­esting frameworks and functional materials since they have multiple coordination nodes to meet the needs of different metal atoms (Chae et al., 2003; Lee et al., 2005; Koh et al., 2010). Furthermore, multiple ligands which contain different coordinated atoms can result in greater tunability of the structural networks than single ligands (Lee et al., 2011). For a better understanding of the intrinsic coordination of multiple ligands and to explore further their influence on the structure of MOFs, we report here the synthesis and crystal structure of a novel MOF incorporating zinc(II), H3TCA and 4,4'-bi­pyridine (bipy), namely [Zn3(TCA)2(bipy)1.5(DMF)2]n, (I).

Experimental top

Synthesis and crystallization top

4,4',4''-Nitrilo­tri­benzoic acid (H3TCA) was synthesized according to the literature method of Dapperheld et al. (1991). H3TCA (0.037 g, 0.10 mmol), Zn(NO3)3·6H2O (0.028 g, 0.10 mmol) and bipy (0.016 g, 0.10 mmol) were dissolved in di­methyl­formamide (DMF; 6 ml). The mixture was sealed and heated to 373 K for 3 d and then cooled to room temperature. Light-yellow rod-like crystals of (I) were collected (yield 39.1%, based on Zn). FT–IR (KBr, ν, cm-1): 1660 (m), 1592 (vs), 1539 (m), 1506 (m), 1393 (vs), 1312 (vs), 1272 (m), 1170 (s), 1099 (w), 1073 (w), 1013 (w), 853 (m), 819 (w), 780 (vs), 712 (w), 675 (m), 639 (w), 526 (m), 457 (w).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The DMF/H2O solvent molecules were highly disordered and we were unsuccessful in locating and refining the solvent peaks. The diffuse electron densities resulting from these residual solvent molecules were removed from the data set using the SQUEEZE routine (Spek, 2015) of PLATON (Spek, 2009) and refined further using the data generated. The final formula does not include the contribution of the solvents. The pyridine ring (N2/C6–C10) and two coordinated DMF molecules (O1/N7/C64–C66 and O14/N6/C61–C63) were also highly disordered and a PART instruction was used to obtain two different positions, which were finally refined with an FVAR value of 0.565260 [Please reword without SHELX specific instructions]. All H atoms were placed in geometrically idealized positions and refined using a riding model, with C—H = 0.96 (methyl), 0.93 (benzene) or 0.93 Å (pyridine), and with Uiso(H) = 1.2Ueq(C) for pyridine and benzene H atoms or 1.5Ueq(C) for methyl H atoms.

Results and discussion top

Light-yellow crystals of (I) were assembled by the solvothermal method in the presence of di­methyl­formamide (DMF) and water. Single-crystal X-ray diffraction analysis reveals that (I) crystallizes in the triclinic P1 space group. The asymmetric unit contains three crystallographically independent ZnII cations, two 4,4',4''-nitrilo­tribenzoate (TCA3-) ligands, one and a half 4,4'-bi­pyridine (bipy) ligands and two coordinated DMF molecules (Fig. 1).

As shown in Fig. 2, atom Zn1 is tetra­coordinated by three O-atom donors from two separate TCA3- ligands, a DMF molecule in a monodentate coordination mode and a pyridine N-atom donor from a bipy molecule, resulting in a slightly distorted tetra­hedral geometry. The Zn—O(TCA3-), Zn—O(DMF) and Zn—N(bipy) bond lengths (Table 2) are comparable with reported literature values (Chang et al., 2014; Yang et al.,2010; Mossine et al., 2014; Fang et al., 2006). The X—Zn—X (X is a basal O or N atom) angles in the distorted tetra­hedron range from 96.690 (2) to 136.516 (1)° and the tetra­hedron edge lengths range from 2.9998 (4) to 3.6230 (5) Å.

Inter­estingly, this framework also contains secondary building units (SBUs) of two penta­coordinated Zn2 cations bridged in a paddle-wheel-type configuration, where two Zn2 atoms occupy the equatorial sites of the o­cta­hedron (Köberl et al., 2011; Tan et al., 2012; Song et al., 2012). The binuclear zinc clusters are coordinated by eight carboxyl­ate O-atom donors from four separate TCA3- ligands in chelating modes and by two pyridine N-atom donors from two different bipy molecules (Table 2).

Atom Zn3 is hexacoordinated by four carboxyl­ate O-atom donors from two separate TCA3- ligands in chelating modes, by another O-atom donor from a DMF molecule and by a pyridine N-atom donor from a bipy molecule. The Zn—O/N bond lengths (Table 2) are comparable with literature values (Chang et al., 2014; Yang et al., 2010; Mossine et al., 2014; Fang et al., 2006).

The binuclear Zn2(COO)4(bipy)2 clusters and bipy molecules are connected in a head-to-tail fashion into an infinite one-dimensional linear chain, with a cluster separation of 13.9620 (2) Å, which is the basis for the extension of the dimensionality. Meanwhile, each paddle-wheel cluster as a 6-connected SBU coordinates to four 3-connected TCA3- ligands and two bipy molecules, forming a larger chain structure. As shown in Fig. 3, the bipy ligands (red) link adjacent layers by coordinating to Zn1 atoms, which further aggregates the structure into a two-dimensional supra­molecular framework.

As shown in Figs. 4(a) and 4(b), the two-dimensional networks can also be inter­digitated with each other along the ac plane, which corresponds to the topological structure. Atoms Zn1 and Zn3 and the TCA3- ligands are considered as 3-connected nodes, while the binuclear Zn2(COO)4(bipy)2 cluster serves as a 6-connected node. Thus, the structure of (I) can be reduced to the new topology of a (3,3,6)-connected 3-nodal net, with the Schläfli symbol {5.62}4{52.6}4{58.87} (see Figs. 4c and 4d), as calculated by the TOPOS software (Blatov, 2006).

In summary, in this work a novel MOF, {[Zn3(TCA)2(bipy)1.5(DMF)2]·(Solvents)}n, with a new topology was obtained by the solvothermal method. It possesses three kinds of crystallographically independent ZnII cations, including binuclear Zn2(COO)4(bipy)2 paddle-wheel clusters. As a result, the two simple ligands may inspire the design of functional MOFs and lay a foundation for our future work.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms and C-atom labels have been omitted for clarity. [Please provide revised plot with the asymmetric unit fully labelled]
[Figure 2] Fig. 2. The coordination environments of atoms Zn1, Zn2 and Zn3 of (I). [Very similar to Fig. 1; is it needed?]
[Figure 3] Fig. 3. A view of the one-dimensional linear structure and two-dimensional framework of (I).
[Figure 4] Fig. 4. (a) The monolayer structure of (I), along the ac plane. (b) The topological structure of the monolayer. (c) The two-dimensional interdigitated structure along the ac plane. (d) An illustration of the topological structure of (I). [Please provide higher-resolution images for parts (a) and (c)]
Poly[sesqui(µ2-4,4'-bipyridine)bis(dimethylformamide)bis(µ4-4,4',4''-nitrilotribenzoato)trizinc(II)] top
Crystal data top
[Zn3(C21H12NO6)2(C10H8N2)1.5(C3H7NO)2]Z = 2
Mr = 1325.21F(000) = 1358
Triclinic, P1Dx = 0.874 Mg m3
a = 13.6198 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.962 (2) ÅCell parameters from 8006 reflections
c = 26.646 (4) Åθ = 2.2–23.4°
α = 85.035 (2)°µ = 0.75 mm1
β = 89.776 (2)°T = 296 K
γ = 86.223 (2)°Rod, light yellow
V = 5037.1 (12) Å30.24 × 0.22 × 0.19 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
11697 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
φ and ω scansθmax = 27.5°, θmin = 0.8°
Absorption correction: ψ scan
(SADABS; Bruker, 2000)
h = 1615
Tmin = 0.830, Tmax = 0.872k = 1717
39611 measured reflectionsl = 3332
20086 independent reflections
Refinement top
Refinement on F2319 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.216 w = 1/[σ2(Fo2) + (0.1184P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.003
20086 reflectionsΔρmax = 1.04 e Å3
859 parametersΔρmin = 1.82 e Å3
Crystal data top
[Zn3(C21H12NO6)2(C10H8N2)1.5(C3H7NO)2]γ = 86.223 (2)°
Mr = 1325.21V = 5037.1 (12) Å3
Triclinic, P1Z = 2
a = 13.6198 (19) ÅMo Kα radiation
b = 13.962 (2) ŵ = 0.75 mm1
c = 26.646 (4) ÅT = 296 K
α = 85.035 (2)°0.24 × 0.22 × 0.19 mm
β = 89.776 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
20086 independent reflections
Absorption correction: ψ scan
(SADABS; Bruker, 2000)
11697 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 0.872Rint = 0.035
39611 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.071319 restraints
wR(F2) = 0.216H-atom parameters constrained
S = 1.06Δρmax = 1.04 e Å3
20086 reflectionsΔρmin = 1.82 e Å3
859 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C11.0975 (4)0.9884 (4)0.2840 (2)0.0695 (14)
H11.14430.93770.28100.083*
C21.0504 (4)0.9963 (4)0.32995 (18)0.0661 (14)
H21.06490.95030.35670.079*
C30.9820 (4)1.0720 (3)0.33598 (17)0.0537 (11)
C40.9645 (5)1.1372 (4)0.2952 (2)0.0769 (17)
H40.92001.19010.29750.092*
C51.0137 (4)1.1242 (4)0.2505 (2)0.0758 (16)
H51.00061.16980.22330.091*
C60.9300 (4)1.0816 (3)0.38349 (17)0.0562 (12)
C70.9243 (9)1.0017 (8)0.4190 (4)0.075 (3)0.575 (2)
H70.95490.94220.41310.091*0.575 (2)
C80.8718 (9)1.0133 (7)0.4634 (4)0.076 (3)0.575 (2)
H80.86720.96010.48660.091*0.575 (2)
C90.8479 (10)1.1710 (7)0.4439 (4)0.084 (3)0.575 (2)
H90.82841.23170.45360.101*0.575 (2)
C100.8966 (10)1.1679 (8)0.3979 (4)0.087 (3)0.575 (2)
H100.90571.22420.37750.104*0.575 (2)
C7'0.9670 (11)1.0537 (13)0.4278 (6)0.085 (4)0.425 (2)
H7'1.02931.02230.43100.102*0.425 (2)
C8'0.9105 (14)1.0724 (15)0.4712 (6)0.099 (5)0.425 (2)
H8'0.94421.06230.50170.119*0.425 (2)
C9'0.7852 (12)1.1364 (12)0.4296 (5)0.082 (4)0.425 (2)
H9'0.72191.16570.43000.099*0.425 (2)
C10'0.8338 (12)1.1325 (12)0.3840 (5)0.087 (4)0.425 (2)
H10'0.80541.16180.35440.104*0.425 (2)
C110.7474 (4)0.9460 (4)0.6098 (2)0.0656 (14)
C120.7767 (4)0.8463 (3)0.63167 (17)0.0567 (12)
C130.8321 (4)0.7809 (4)0.60504 (18)0.0719 (15)
H130.84990.79940.57210.086*
C140.8615 (4)0.6903 (3)0.62528 (18)0.0722 (15)
H140.89950.64860.60660.087*
C150.8337 (4)0.6615 (3)0.67431 (16)0.0591 (13)
C160.7778 (4)0.7256 (4)0.70131 (17)0.0695 (15)
H160.75780.70650.73390.083*
C170.7518 (4)0.8160 (4)0.68084 (19)0.0661 (14)
H170.71650.85870.70020.079*
C180.8269 (5)0.2378 (4)0.58557 (19)0.0720 (16)
C190.8387 (5)0.3267 (3)0.61331 (19)0.0670 (14)
C200.9186 (5)0.3338 (4)0.6401 (2)0.0866 (19)
H200.96850.28490.64110.104*
C210.9297 (5)0.4145 (4)0.6674 (2)0.0835 (18)
H210.98710.41860.68560.100*
C220.8579 (4)0.4860 (3)0.66723 (16)0.0592 (13)
C230.7732 (5)0.4782 (4)0.6397 (2)0.0893 (19)
H230.72190.52570.63950.107*
C240.7656 (5)0.3986 (4)0.6125 (2)0.0861 (18)
H240.70950.39420.59320.103*
C250.9709 (3)0.5129 (3)0.90358 (15)0.0428 (10)
C260.9504 (3)0.5261 (3)0.84824 (15)0.0425 (9)
C270.9684 (4)0.6094 (3)0.81923 (17)0.0582 (12)
H270.99680.65880.83400.070*
C280.9455 (4)0.6209 (3)0.76953 (18)0.0682 (15)
H280.96240.67620.75040.082*
C290.8964 (4)0.5507 (3)0.74632 (15)0.0524 (11)
C300.8786 (4)0.4684 (3)0.77520 (17)0.0607 (13)
H300.84750.42010.76090.073*
C310.9056 (4)0.4554 (3)0.82499 (16)0.0553 (12)
H310.89370.39780.84350.066*
C320.8139 (3)0.5131 (3)1.01971 (16)0.0460 (10)
C330.7122 (3)0.5206 (3)1.04053 (17)0.0465 (10)
C340.6508 (3)0.4446 (3)1.03816 (18)0.0547 (12)
H340.67390.38991.02300.066*
C350.5591 (3)0.4487 (3)1.05725 (19)0.0600 (13)
H350.51840.39901.05310.072*
C360.5241 (3)0.5268 (3)1.08328 (18)0.0529 (11)
C370.5867 (3)0.6015 (3)1.0858 (2)0.0629 (14)
H370.56550.65491.10240.075*
C380.6764 (3)0.5986 (3)1.0649 (2)0.0616 (13)
H380.71530.65041.06690.074*
C390.2298 (4)0.8875 (4)1.1443 (2)0.0648 (14)
C400.2799 (3)0.7928 (3)1.13407 (19)0.0561 (12)
C410.3250 (4)0.7814 (3)1.08790 (19)0.0593 (12)
H410.32250.83291.06320.071*
C420.3730 (3)0.6956 (3)1.07803 (18)0.0557 (12)
H420.40110.68911.04650.067*
C430.3800 (3)0.6186 (3)1.11460 (18)0.0522 (11)
C440.3331 (4)0.6268 (3)1.1605 (2)0.0681 (14)
H440.33510.57541.18520.082*
C450.2820 (4)0.7157 (4)1.1686 (2)0.0704 (15)
H450.24850.72131.19880.085*
C460.2456 (4)0.1806 (3)1.16346 (18)0.0521 (11)
C470.2944 (3)0.2725 (3)1.14869 (17)0.0498 (11)
C480.2476 (3)0.3442 (3)1.11651 (17)0.0473 (10)
H480.18510.33591.10430.057*
C490.2931 (3)0.4285 (3)1.10233 (18)0.0535 (11)
H490.26130.47591.08040.064*
C500.3839 (3)0.4419 (3)1.12031 (18)0.0527 (11)
C510.4320 (4)0.3694 (4)1.1516 (2)0.0682 (14)
H510.49520.37711.16320.082*
C520.3863 (3)0.2861 (4)1.1657 (2)0.0636 (13)
H520.41880.23831.18710.076*
C561.0602 (4)0.1966 (3)1.0269 (2)0.0800 (19)
H561.10540.22451.04620.096*
C571.0655 (4)0.0962 (3)1.0272 (2)0.0702 (16)
H571.11390.05911.04600.084*
C580.9997 (3)0.0528 (2)0.99990 (15)0.0403 (9)
C590.9313 (4)0.1132 (3)0.9735 (2)0.0724 (17)
H590.88490.08710.95400.087*
C600.9296 (4)0.2122 (3)0.9750 (2)0.0696 (16)
H600.88100.25090.95730.083*
O140.0039 (3)0.0471 (4)1.13691 (17)0.05665 (17)0.575 (2)
C610.0424 (5)0.1225 (5)1.12665 (19)0.05665 (17)0.575 (2)
H610.00850.17751.12950.068*0.575 (2)
C620.1931 (6)0.2260 (5)1.0970 (3)0.05665 (17)0.575 (2)
H62A0.15040.27551.10350.085*0.575 (2)
H62B0.25130.23211.11720.085*0.575 (2)
H62C0.21110.23221.06200.085*0.575 (2)
C630.1858 (5)0.0413 (5)1.1068 (3)0.05665 (17)0.575 (2)
H63A0.15830.00961.07890.085*0.575 (2)
H63B0.25560.05311.10220.085*0.575 (2)
H63C0.17300.00111.13750.085*0.575 (2)
N60.1418 (4)0.1309 (4)1.10970 (17)0.05665 (17)0.575 (2)
N70.4615 (6)1.1508 (4)0.5010 (3)0.0982 (7)0.575 (2)
O10.6145 (5)1.1075 (7)0.5079 (4)0.0950 (6)0.575 (2)
C640.5499 (6)1.1400 (6)0.5320 (3)0.0967 (6)0.575 (2)
H640.55451.15590.56500.116*0.575 (2)
C650.3675 (6)1.1887 (8)0.5185 (4)0.1008 (8)0.575 (2)
H65A0.35831.16510.55300.151*0.575 (2)
H65B0.31591.16850.49820.151*0.575 (2)
H65C0.36591.25780.51590.151*0.575 (2)
C660.4678 (7)1.1209 (8)0.4485 (3)0.1003 (8)0.575 (2)
H66A0.40381.10600.43770.150*0.575 (2)
H66B0.51261.06510.44770.150*0.575 (2)
H66C0.49101.17260.42640.150*0.575 (2)
O14'0.0037 (4)0.0044 (5)1.1471 (3)0.05665 (17)0.425 (2)
N6'0.0919 (6)0.1225 (5)1.1278 (2)0.05665 (17)0.425 (2)
C61'0.0022 (7)0.0871 (6)1.1451 (3)0.05665 (17)0.425 (2)
H61'0.05090.12991.15460.068*0.425 (2)
C62'0.0990 (8)0.2271 (6)1.1323 (3)0.05665 (17)0.425 (2)
H62D0.03740.25801.12290.085*0.425 (2)
H62E0.15020.24331.11060.085*0.425 (2)
H62F0.11390.24851.16660.085*0.425 (2)
C63'0.1595 (6)0.0420 (6)1.1087 (3)0.05665 (17)0.425 (2)
H63D0.19120.01321.13650.085*0.425 (2)
H63E0.20830.06511.08770.085*0.425 (2)
H63F0.12340.00511.08940.085*0.425 (2)
N7'0.4357 (7)1.0990 (6)0.5094 (3)0.0981 (7)0.425 (2)
O1'0.6012 (6)1.1170 (11)0.5102 (5)0.0952 (7)0.425 (2)
C64'0.5376 (7)1.0680 (7)0.5288 (4)0.0965 (6)0.425 (2)
H64'0.55061.01630.55280.116*0.425 (2)
C65'0.3509 (7)1.0582 (9)0.5307 (5)0.1008 (9)0.425 (2)
H65D0.29401.08240.51120.151*0.425 (2)
H65E0.34281.07540.56460.151*0.425 (2)
H65F0.35830.98940.53070.151*0.425 (2)
C66'0.4331 (8)1.1746 (9)0.4667 (5)0.0995 (8)0.425 (2)
H66D0.38401.16190.44280.149*0.425 (2)
H66E0.49631.17460.45060.149*0.425 (2)
H66F0.41751.23640.47900.149*0.425 (2)
N11.0781 (3)1.0514 (3)0.24378 (14)0.0547 (10)
N20.8276 (4)1.0986 (3)0.47397 (14)0.0603 (10)
N30.8668 (4)0.5660 (3)0.69583 (14)0.0702 (12)
N40.4301 (3)0.5300 (3)1.10522 (16)0.0604 (11)
N50.9953 (3)0.2532 (2)1.00092 (13)0.0419 (8)
O20.7863 (3)0.9696 (2)0.56683 (13)0.0738 (10)
O30.6916 (4)0.9997 (3)0.63188 (16)0.1009 (14)
O40.8949 (4)0.1780 (3)0.58218 (15)0.0989 (14)
O50.7436 (3)0.2279 (3)0.56677 (15)0.0869 (12)
O60.9862 (2)0.5879 (2)0.92502 (10)0.0509 (7)
O70.9706 (2)0.4304 (2)0.92470 (11)0.0575 (8)
O80.8600 (2)0.5892 (2)1.01408 (13)0.0593 (8)
O90.8494 (2)0.4319 (2)1.01005 (12)0.0553 (8)
O100.2204 (3)0.9549 (3)1.11119 (16)0.0743 (10)
O110.1943 (3)0.8961 (3)1.18808 (16)0.0877 (12)
O120.2863 (3)0.1169 (2)1.19227 (14)0.0710 (10)
O130.1611 (2)0.1699 (2)1.14417 (12)0.0576 (8)
Zn10.75053 (4)1.10165 (4)0.54052 (2)0.05677 (17)
Zn20.99475 (3)0.39776 (3)0.99981 (2)0.03428 (13)
Zn30.14112 (4)0.03622 (4)1.17412 (2)0.05665 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.080 (4)0.059 (3)0.067 (3)0.009 (3)0.013 (3)0.001 (3)
C20.086 (4)0.062 (3)0.049 (3)0.001 (3)0.005 (3)0.002 (2)
C30.071 (3)0.043 (3)0.048 (3)0.006 (2)0.005 (2)0.005 (2)
C40.111 (5)0.055 (3)0.060 (3)0.022 (3)0.022 (3)0.000 (2)
C50.109 (5)0.051 (3)0.063 (3)0.009 (3)0.024 (3)0.009 (2)
C60.069 (3)0.051 (3)0.049 (3)0.002 (2)0.006 (2)0.012 (2)
C70.102 (7)0.058 (5)0.062 (5)0.016 (5)0.018 (5)0.001 (4)
C80.108 (7)0.056 (5)0.057 (5)0.018 (5)0.019 (5)0.011 (4)
C90.119 (7)0.052 (5)0.079 (6)0.006 (5)0.031 (6)0.005 (5)
C100.113 (7)0.064 (6)0.080 (6)0.006 (5)0.034 (6)0.000 (5)
C7'0.071 (7)0.117 (9)0.063 (7)0.001 (7)0.009 (6)0.001 (7)
C8'0.099 (9)0.127 (10)0.071 (8)0.002 (8)0.012 (7)0.008 (7)
C9'0.076 (7)0.102 (8)0.064 (7)0.023 (7)0.011 (6)0.001 (6)
C10'0.094 (8)0.100 (8)0.060 (7)0.017 (7)0.007 (6)0.014 (6)
C110.086 (4)0.052 (3)0.059 (3)0.002 (3)0.011 (3)0.009 (3)
C120.075 (3)0.049 (3)0.047 (3)0.010 (2)0.006 (2)0.002 (2)
C130.121 (5)0.051 (3)0.043 (3)0.004 (3)0.001 (3)0.001 (2)
C140.123 (5)0.045 (3)0.047 (3)0.003 (3)0.006 (3)0.003 (2)
C150.100 (4)0.035 (2)0.042 (2)0.000 (2)0.014 (2)0.0047 (19)
C160.115 (5)0.057 (3)0.036 (2)0.004 (3)0.007 (3)0.003 (2)
C170.080 (4)0.064 (3)0.054 (3)0.003 (3)0.002 (3)0.009 (2)
C180.119 (5)0.050 (3)0.047 (3)0.004 (3)0.000 (3)0.007 (2)
C190.103 (4)0.043 (3)0.056 (3)0.000 (3)0.011 (3)0.010 (2)
C200.114 (5)0.068 (4)0.077 (4)0.025 (3)0.020 (4)0.026 (3)
C210.095 (4)0.086 (4)0.072 (4)0.007 (3)0.026 (3)0.032 (3)
C220.093 (4)0.045 (3)0.040 (2)0.001 (3)0.009 (2)0.009 (2)
C230.116 (5)0.057 (3)0.097 (5)0.020 (3)0.031 (4)0.031 (3)
C240.106 (5)0.068 (4)0.088 (4)0.004 (3)0.031 (4)0.029 (3)
C250.048 (2)0.036 (2)0.045 (2)0.0019 (19)0.0031 (19)0.0089 (19)
C260.053 (3)0.033 (2)0.042 (2)0.0038 (18)0.0004 (19)0.0055 (17)
C270.090 (4)0.038 (2)0.049 (3)0.019 (2)0.013 (2)0.006 (2)
C280.115 (4)0.044 (3)0.047 (3)0.027 (3)0.005 (3)0.003 (2)
C290.084 (3)0.039 (2)0.035 (2)0.009 (2)0.006 (2)0.0020 (18)
C300.096 (4)0.039 (2)0.049 (3)0.019 (2)0.011 (3)0.007 (2)
C310.084 (3)0.039 (2)0.043 (2)0.008 (2)0.000 (2)0.0019 (19)
C320.047 (3)0.045 (3)0.046 (2)0.002 (2)0.0021 (19)0.0053 (19)
C330.043 (2)0.038 (2)0.059 (3)0.0065 (19)0.001 (2)0.0045 (19)
C340.055 (3)0.042 (2)0.070 (3)0.010 (2)0.010 (2)0.019 (2)
C350.058 (3)0.041 (3)0.085 (4)0.019 (2)0.015 (3)0.020 (2)
C360.048 (3)0.038 (2)0.073 (3)0.008 (2)0.006 (2)0.005 (2)
C370.055 (3)0.035 (2)0.103 (4)0.009 (2)0.011 (3)0.026 (2)
C380.049 (3)0.044 (3)0.096 (4)0.019 (2)0.021 (3)0.023 (3)
C390.057 (3)0.053 (3)0.090 (4)0.014 (3)0.006 (3)0.030 (3)
C400.057 (3)0.038 (2)0.077 (3)0.012 (2)0.008 (2)0.018 (2)
C410.066 (3)0.046 (3)0.066 (3)0.008 (2)0.004 (2)0.008 (2)
C420.055 (3)0.048 (3)0.064 (3)0.002 (2)0.010 (2)0.011 (2)
C430.046 (3)0.043 (3)0.070 (3)0.007 (2)0.011 (2)0.015 (2)
C440.086 (4)0.039 (3)0.081 (4)0.013 (3)0.023 (3)0.007 (2)
C450.082 (4)0.051 (3)0.082 (4)0.012 (3)0.030 (3)0.026 (3)
C460.068 (3)0.037 (2)0.052 (3)0.009 (2)0.017 (2)0.009 (2)
C470.054 (3)0.041 (2)0.055 (3)0.008 (2)0.010 (2)0.006 (2)
C480.046 (2)0.037 (2)0.060 (3)0.0050 (19)0.001 (2)0.006 (2)
C490.052 (3)0.037 (2)0.069 (3)0.002 (2)0.003 (2)0.002 (2)
C500.046 (3)0.042 (2)0.070 (3)0.006 (2)0.011 (2)0.006 (2)
C510.053 (3)0.054 (3)0.096 (4)0.015 (2)0.014 (3)0.008 (3)
C520.052 (3)0.060 (3)0.076 (3)0.001 (2)0.009 (2)0.012 (3)
C560.101 (4)0.022 (2)0.118 (5)0.007 (2)0.067 (4)0.005 (3)
C570.089 (4)0.019 (2)0.101 (4)0.005 (2)0.050 (3)0.002 (2)
C580.056 (3)0.0167 (19)0.048 (2)0.0025 (17)0.0116 (19)0.0021 (16)
C590.092 (4)0.022 (2)0.105 (4)0.003 (2)0.053 (3)0.012 (2)
C600.086 (4)0.021 (2)0.101 (4)0.002 (2)0.053 (3)0.001 (2)
O140.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
C610.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
C620.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
C630.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
N60.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
N70.0952 (7)0.0995 (9)0.0996 (8)0.0063 (6)0.0019 (5)0.0078 (6)
O10.0917 (7)0.0970 (9)0.0965 (8)0.0073 (6)0.0037 (5)0.0086 (6)
C640.0933 (7)0.0983 (8)0.0985 (8)0.0066 (5)0.0018 (5)0.0083 (5)
C650.0964 (9)0.1028 (12)0.1026 (12)0.0051 (9)0.0010 (9)0.0073 (10)
C660.0986 (12)0.1019 (13)0.1003 (10)0.0061 (10)0.0029 (8)0.0091 (10)
O14'0.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
N6'0.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
C61'0.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
C62'0.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
C63'0.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
N7'0.0949 (7)0.0994 (8)0.0998 (8)0.0068 (5)0.0016 (5)0.0079 (5)
O1'0.0920 (7)0.0971 (9)0.0967 (9)0.0067 (6)0.0033 (6)0.0086 (6)
C64'0.0932 (7)0.0981 (8)0.0982 (8)0.0074 (5)0.0022 (5)0.0083 (5)
C65'0.0955 (10)0.1033 (14)0.1034 (14)0.0070 (11)0.0003 (11)0.0078 (11)
C66'0.0974 (11)0.1009 (12)0.1000 (11)0.0049 (9)0.0019 (9)0.0075 (8)
N10.076 (3)0.038 (2)0.052 (2)0.0065 (19)0.0119 (19)0.0101 (17)
N20.085 (3)0.049 (2)0.047 (2)0.004 (2)0.009 (2)0.0076 (18)
N30.123 (4)0.046 (2)0.044 (2)0.015 (2)0.019 (2)0.0084 (18)
N40.046 (2)0.038 (2)0.099 (3)0.0072 (17)0.021 (2)0.009 (2)
N50.059 (2)0.0135 (14)0.053 (2)0.0007 (14)0.0111 (17)0.0032 (14)
O20.114 (3)0.046 (2)0.060 (2)0.0093 (19)0.001 (2)0.0081 (16)
O30.141 (4)0.073 (3)0.082 (3)0.028 (3)0.012 (3)0.003 (2)
O40.155 (4)0.060 (2)0.082 (3)0.020 (3)0.023 (3)0.026 (2)
O50.115 (3)0.066 (3)0.085 (3)0.012 (2)0.006 (3)0.030 (2)
O60.065 (2)0.0456 (17)0.0428 (16)0.0061 (15)0.0043 (14)0.0074 (13)
O70.089 (2)0.0404 (18)0.0421 (17)0.0018 (16)0.0046 (16)0.0007 (13)
O80.0486 (18)0.0479 (19)0.082 (2)0.0105 (15)0.0117 (16)0.0031 (16)
O90.0495 (18)0.0450 (18)0.072 (2)0.0014 (14)0.0020 (15)0.0122 (15)
O100.073 (2)0.045 (2)0.106 (3)0.0045 (18)0.015 (2)0.017 (2)
O110.115 (3)0.056 (2)0.095 (3)0.004 (2)0.023 (2)0.031 (2)
O120.083 (2)0.049 (2)0.077 (2)0.0045 (18)0.002 (2)0.0140 (18)
O130.066 (2)0.0439 (18)0.065 (2)0.0143 (16)0.0052 (17)0.0058 (15)
Zn10.0839 (4)0.0422 (3)0.0447 (3)0.0037 (3)0.0030 (3)0.0071 (2)
Zn20.0454 (3)0.0147 (2)0.0431 (3)0.00318 (17)0.0004 (2)0.00419 (17)
Zn30.0716 (4)0.0410 (3)0.0603 (3)0.0153 (3)0.0186 (3)0.0127 (2)
Geometric parameters (Å, º) top
C1—N11.342 (6)C44—C451.415 (6)
C1—C21.390 (7)C44—H440.9300
C1—H10.9300C45—H450.9300
C2—C31.382 (6)C46—O121.229 (5)
C2—H20.9300C46—O131.284 (6)
C3—C41.367 (6)C46—C471.505 (6)
C3—C61.460 (6)C46—Zn32.539 (5)
C4—C51.385 (7)C47—C521.364 (6)
C4—H40.9300C47—C481.384 (6)
C5—N11.321 (6)C48—C491.390 (6)
C5—H50.9300C48—H480.9300
C6—C7'1.303 (15)C49—C501.357 (6)
C6—C101.347 (11)C49—H490.9300
C6—C71.405 (11)C50—C511.386 (6)
C6—C10'1.450 (15)C50—N41.445 (5)
C7—C81.395 (13)C51—C521.378 (6)
C7—H70.9300C51—H510.9300
C8—N21.351 (10)C52—H520.9300
C8—H80.9300C56—N51.305 (5)
C9—N21.280 (11)C56—C571.398 (6)
C9—C101.394 (14)C56—H560.9300
C9—H90.9300C57—C581.361 (6)
C10—H100.9300C57—H570.9300
C7'—C8'1.42 (2)C58—C591.369 (6)
C7'—H7'0.9300C58—C58ii1.473 (7)
C8'—N21.168 (18)C59—C601.386 (6)
C8'—H8'0.9300C59—H590.9300
C9'—N21.367 (15)C60—N51.321 (5)
C9'—C10'1.384 (18)C60—H600.9300
C9'—H9'0.9300O14—C611.156 (7)
C10'—H10'0.9300O14—Zn32.204 (5)
C11—O31.219 (6)C61—N61.424 (7)
C11—O21.285 (6)C61—H610.9300
C11—C121.492 (7)C62—N61.471 (7)
C12—C171.389 (6)C62—H62A0.9600
C12—C131.387 (7)C62—H62B0.9600
C13—C141.366 (7)C62—H62C0.9600
C13—H130.9300C63—N61.431 (7)
C14—C151.392 (6)C63—H63A0.9600
C14—H140.9300C63—H63B0.9600
C15—C161.384 (6)C63—H63C0.9600
C15—N31.449 (6)N7—C651.444 (7)
C16—C171.356 (7)N7—C641.455 (8)
C16—H160.9300N7—C661.493 (8)
C17—H170.9300O1—C641.177 (8)
C18—O41.214 (7)O1—Zn12.042 (6)
C18—O51.263 (7)C64—H640.9300
C18—C191.515 (7)C65—H65A0.9600
C19—C201.319 (8)C65—H65B0.9600
C19—C241.366 (7)C65—H65C0.9600
C20—C211.407 (7)C66—H66A0.9600
C20—H200.9300C66—H66B0.9600
C21—C221.351 (7)C66—H66C0.9600
C21—H210.9300O14'—C61'1.168 (8)
C22—C231.385 (7)O14'—Zn32.136 (6)
C22—N31.417 (6)N6'—C61'1.439 (8)
C23—C241.389 (7)N6'—C63'1.462 (8)
C23—H230.9300N6'—C62'1.465 (8)
C24—H240.9300C61'—H61'0.9300
C25—O71.238 (5)C62'—H62D0.9600
C25—O61.264 (5)C62'—H62E0.9600
C25—C261.495 (6)C62'—H62F0.9600
C26—C271.375 (6)C63'—H63D0.9600
C26—C311.385 (6)C63'—H63E0.9600
C27—C281.355 (6)C63'—H63F0.9600
C27—H270.9300N7'—C65'1.416 (8)
C28—C291.408 (6)N7'—C64'1.507 (8)
C28—H280.9300N7'—C66'1.482 (8)
C29—C301.361 (6)O1'—C64'1.218 (9)
C29—N31.401 (5)O1'—Zn12.182 (7)
C30—C311.372 (6)C64'—H64'0.9300
C30—H300.9300C65'—H65D0.9600
C31—H310.9300C65'—H65E0.9600
C32—O91.250 (5)C65'—H65F0.9600
C32—O81.266 (5)C66'—H66D0.9600
C32—C331.491 (6)C66'—H66E0.9600
C33—C381.377 (6)C66'—H66F0.9600
C33—C341.399 (6)N1—Zn3iii2.064 (4)
C34—C351.347 (6)N2—Zn12.059 (4)
C34—H340.9300N5—Zn22.015 (3)
C35—C361.399 (6)O2—Zn11.946 (3)
C35—H350.9300O5—Zn1iv1.949 (4)
C36—C371.396 (6)O6—Zn2v2.049 (3)
C36—N41.404 (5)O7—Zn22.037 (3)
C37—C381.340 (6)O8—Zn2v2.029 (3)
C37—H370.9300O9—Zn22.028 (3)
C38—H380.9300O10—Zn3i2.328 (4)
C39—O101.233 (6)O11—Zn3i2.044 (4)
C39—O111.274 (6)O12—Zn32.410 (4)
C39—C401.493 (6)O13—Zn32.001 (3)
C39—Zn3i2.520 (5)Zn1—O5i1.949 (4)
C40—C451.353 (7)Zn2—O8v2.029 (3)
C40—C411.389 (6)Zn2—O6v2.049 (3)
C41—C421.372 (6)Zn2—Zn2v2.8689 (9)
C41—H410.9300Zn3—O11iv2.044 (4)
C42—C431.386 (6)Zn3—N1vi2.064 (4)
C42—H420.9300Zn3—O10iv2.328 (4)
C43—C441.388 (6)Zn3—C39iv2.520 (5)
C43—N41.414 (5)
N1—C1—C2122.4 (5)N5—C56—H56118.2
N1—C1—H1118.8C57—C56—H56118.2
C2—C1—H1118.8C58—C57—C56119.8 (4)
C3—C2—C1120.3 (5)C58—C57—H57120.1
C3—C2—H2119.9C56—C57—H57120.1
C1—C2—H2119.9C57—C58—C59115.9 (3)
C4—C3—C2116.9 (4)C57—C58—C58ii121.9 (4)
C4—C3—C6121.4 (4)C59—C58—C58ii122.2 (5)
C2—C3—C6121.7 (4)C58—C59—C60121.5 (4)
C3—C4—C5119.6 (5)C58—C59—H59119.3
C3—C4—H4120.2C60—C59—H59119.3
C5—C4—H4120.2N5—C60—C59121.8 (4)
N1—C5—C4124.3 (5)N5—C60—H60119.1
N1—C5—H5117.8C59—C60—H60119.1
C4—C5—H5117.8C61—O14—Zn3119.0 (5)
C10—C6—C7117.0 (7)O14—C61—N6119.8 (7)
C7'—C6—C10'114.9 (9)O14—C61—H61120.1
C7'—C6—C3124.6 (8)N6—C61—H61120.1
C10—C6—C3122.0 (6)N6—C62—H62A109.5
C7—C6—C3120.5 (5)N6—C62—H62B109.5
C10'—C6—C3120.2 (7)H62A—C62—H62B109.5
C8—C7—C6118.7 (8)N6—C62—H62C109.5
C8—C7—H7120.6H62A—C62—H62C109.5
C6—C7—H7120.6H62B—C62—H62C109.5
N2—C8—C7122.7 (8)N6—C63—H63A109.5
N2—C8—H8118.6N6—C63—H63B109.5
C7—C8—H8118.6H63A—C63—H63B109.5
N2—C9—C10126.4 (9)N6—C63—H63C109.5
N2—C9—H9116.8H63A—C63—H63C109.5
C10—C9—H9116.8H63B—C63—H63C109.5
C6—C10—C9118.5 (9)C61—N6—C63114.9 (6)
C6—C10—H10120.7C61—N6—C62121.0 (6)
C9—C10—H10120.7C63—N6—C62124.2 (6)
C6—C7'—C8'118.8 (14)C65—N7—C64123.2 (6)
C6—C7'—H7'120.6C65—N7—C66118.2 (6)
C8'—C7'—H7'120.6C64—N7—C66118.6 (6)
N2—C8'—C7'129.1 (15)C64—O1—Zn1115.1 (6)
N2—C8'—H8'115.5O1—C64—N7108.0 (6)
C7'—C8'—H8'115.5O1—C64—H64126.0
N2—C9'—C10'121.9 (13)N7—C64—H64126.0
N2—C9'—H9'119.0N7—C65—H65A109.5
C10'—C9'—H9'119.0N7—C65—H65B109.5
C9'—C10'—C6118.5 (12)H65A—C65—H65B109.5
C9'—C10'—H10'120.8N7—C65—H65C109.5
C6—C10'—H10'120.8H65A—C65—H65C109.5
O3—C11—O2123.9 (5)H65B—C65—H65C109.5
O3—C11—C12121.4 (5)N7—C66—H66A109.5
O2—C11—C12114.7 (5)N7—C66—H66B109.5
C17—C12—C13116.9 (4)H66A—C66—H66B109.5
C17—C12—C11120.8 (5)N7—C66—H66C109.5
C13—C12—C11122.3 (4)H66A—C66—H66C109.5
C14—C13—C12122.7 (5)H66B—C66—H66C109.5
C14—C13—H13118.7C61'—O14'—Zn3115.3 (7)
C12—C13—H13118.7C61'—N6'—C63'110.1 (7)
C13—C14—C15119.0 (5)C61'—N6'—C62'117.0 (8)
C13—C14—H14120.5C63'—N6'—C62'132.8 (8)
C15—C14—H14120.5O14'—C61'—N6'119.9 (9)
C14—C15—C16119.1 (4)O14'—C61'—H61'120.0
C14—C15—N3118.7 (4)N6'—C61'—H61'120.0
C16—C15—N3122.2 (4)N6'—C62'—H62D109.5
C17—C16—C15120.7 (5)N6'—C62'—H62E109.5
C17—C16—H16119.6H62D—C62'—H62E109.5
C15—C16—H16119.6N6'—C62'—H62F109.5
C16—C17—C12121.5 (5)H62D—C62'—H62F109.5
C16—C17—H17119.2H62E—C62'—H62F109.5
C12—C17—H17119.2N6'—C63'—H63D109.5
O4—C18—O5121.5 (5)N6'—C63'—H63E109.5
O4—C18—C19121.0 (6)H63D—C63'—H63E109.5
O5—C18—C19117.5 (5)N6'—C63'—H63F109.5
C20—C19—C24119.1 (5)H63D—C63'—H63F109.5
C20—C19—C18120.2 (5)H63E—C63'—H63F109.5
C24—C19—C18120.7 (5)C65'—N7'—C64'121.9 (6)
C19—C20—C21121.0 (5)C65'—N7'—C66'124.0 (6)
C19—C20—H20119.5C64'—N7'—C66'114.2 (6)
C21—C20—H20119.5C64'—O1'—Zn1120.5 (8)
C22—C21—C20120.8 (5)O1'—C64'—N7'113.6 (7)
C22—C21—H21119.6O1'—C64'—H64'123.2
C20—C21—H21119.6N7'—C64'—H64'123.2
C21—C22—C23118.5 (5)N7'—C65'—H65D109.5
C21—C22—N3121.2 (5)N7'—C65'—H65E109.5
C23—C22—N3120.2 (5)H65D—C65'—H65E109.5
C22—C23—C24119.3 (5)N7'—C65'—H65F109.5
C22—C23—H23120.4H65D—C65'—H65F109.5
C24—C23—H23120.4H65E—C65'—H65F109.5
C19—C24—C23121.4 (6)N7'—C66'—H66D109.5
C19—C24—H24119.3N7'—C66'—H66E109.5
C23—C24—H24119.3H66D—C66'—H66E109.5
O7—C25—O6125.4 (4)N7'—C66'—H66F109.5
O7—C25—C26117.8 (4)H66D—C66'—H66F109.5
O6—C25—C26116.8 (4)H66E—C66'—H66F109.5
C27—C26—C31117.4 (4)C5—N1—C1116.5 (4)
C27—C26—C25122.5 (4)C5—N1—Zn3iii120.6 (3)
C31—C26—C25120.0 (4)C1—N1—Zn3iii122.9 (3)
C28—C27—C26121.3 (4)C9—N2—C8115.2 (7)
C28—C27—H27119.3C8'—N2—C9'115.0 (11)
C26—C27—H27119.3C8'—N2—Zn1124.2 (9)
C27—C28—C29121.3 (4)C9—N2—Zn1126.9 (5)
C27—C28—H28119.4C8—N2—Zn1117.4 (5)
C29—C28—H28119.4C9'—N2—Zn1120.6 (7)
C30—C29—N3121.9 (4)C29—N3—C22119.6 (4)
C30—C29—C28117.1 (4)C29—N3—C15120.6 (4)
N3—C29—C28121.0 (4)C22—N3—C15119.3 (4)
C29—C30—C31121.4 (4)C36—N4—C43121.2 (4)
C29—C30—H30119.3C36—N4—C50120.3 (4)
C31—C30—H30119.3C43—N4—C50118.4 (3)
C30—C31—C26121.4 (4)C56—N5—C60117.4 (3)
C30—C31—H31119.3C56—N5—Zn2121.7 (3)
C26—C31—H31119.3C60—N5—Zn2120.9 (3)
O9—C32—O8124.0 (4)C11—O2—Zn1113.7 (3)
O9—C32—C33118.1 (4)C18—O5—Zn1iv106.6 (4)
O8—C32—C33117.9 (4)C25—O6—Zn2v128.8 (3)
C38—C33—C34117.3 (4)C25—O7—Zn2123.8 (3)
C38—C33—C32122.4 (4)C32—O8—Zn2v128.4 (3)
C34—C33—C32120.3 (4)C32—O9—Zn2124.6 (3)
C35—C34—C33121.6 (4)C39—O10—Zn3i84.1 (3)
C35—C34—H34119.2C39—O11—Zn3i96.1 (4)
C33—C34—H34119.2C46—O12—Zn381.5 (3)
C34—C35—C36120.9 (4)C46—O13—Zn398.9 (3)
C34—C35—H35119.6O2—Zn1—O5i136.29 (17)
C36—C35—H35119.6O2—Zn1—O1109.0 (3)
C37—C36—C35116.7 (4)O5i—Zn1—O199.2 (3)
C37—C36—N4121.9 (4)O2—Zn1—N297.21 (16)
C35—C36—N4121.4 (4)O5i—Zn1—N2112.91 (17)
C38—C37—C36122.0 (4)O1—Zn1—N295.4 (3)
C38—C37—H37119.0O2—Zn1—O1'111.6 (4)
C36—C37—H37119.0O5i—Zn1—O1'94.7 (4)
C37—C38—C33121.5 (4)N2—Zn1—O1'99.1 (4)
C37—C38—H38119.3N5—Zn2—O9100.62 (13)
C33—C38—H38119.3N5—Zn2—O8v97.88 (13)
O10—C39—O11120.5 (5)O9—Zn2—O8v161.34 (12)
O10—C39—C40121.5 (5)N5—Zn2—O798.21 (13)
O11—C39—C40118.0 (5)O9—Zn2—O787.29 (13)
O10—C39—Zn3i66.8 (3)O8v—Zn2—O787.66 (14)
O11—C39—Zn3i53.8 (3)N5—Zn2—O6v100.14 (13)
C40—C39—Zn3i171.8 (4)O9—Zn2—O6v87.48 (12)
C45—C40—C41118.0 (4)O8v—Zn2—O6v91.69 (13)
C45—C40—C39121.8 (5)O7—Zn2—O6v161.55 (12)
C41—C40—C39120.2 (5)N5—Zn2—Zn2v176.77 (10)
C42—C41—C40121.2 (5)O9—Zn2—Zn2v82.28 (9)
C42—C41—H41119.4O8v—Zn2—Zn2v79.29 (9)
C40—C41—H41119.4O7—Zn2—Zn2v83.31 (8)
C41—C42—C43120.5 (4)O6v—Zn2—Zn2v78.46 (8)
C41—C42—H42119.7O13—Zn3—O11iv148.95 (15)
C43—C42—H42119.7O13—Zn3—N1vi105.89 (14)
C42—C43—C44119.5 (4)O11iv—Zn3—N1vi97.21 (16)
C42—C43—N4121.3 (4)O13—Zn3—O14'107.8 (2)
C44—C43—N4119.2 (4)O11iv—Zn3—O14'92.6 (2)
C43—C44—C45118.0 (5)N1vi—Zn3—O14'89.5 (2)
C43—C44—H44121.0O13—Zn3—O1488.29 (18)
C45—C44—H44121.0O11iv—Zn3—O14111.72 (19)
C40—C45—C44122.6 (5)N1vi—Zn3—O1491.93 (17)
C40—C45—H45118.7O13—Zn3—O10iv97.07 (14)
C44—C45—H45118.7O11iv—Zn3—O10iv59.28 (15)
O12—C46—O13121.0 (4)N1vi—Zn3—O10iv156.33 (15)
O12—C46—C47120.9 (5)O14'—Zn3—O10iv88.9 (2)
O13—C46—C47118.0 (4)O14—Zn3—O10iv94.46 (15)
O12—C46—Zn369.9 (3)O13—Zn3—O1258.59 (12)
O13—C46—Zn351.2 (2)O11iv—Zn3—O1299.75 (15)
C47—C46—Zn3168.9 (4)N1vi—Zn3—O1294.55 (14)
C52—C47—C48118.5 (4)O14'—Zn3—O12166.4 (2)
C52—C47—C46121.0 (4)O14—Zn3—O12146.76 (17)
C48—C47—C46120.5 (4)O10iv—Zn3—O1292.51 (13)
C49—C48—C47120.5 (4)O13—Zn3—C39iv123.62 (17)
C49—C48—H48119.7O11iv—Zn3—C39iv30.17 (17)
C47—C48—H48119.7N1vi—Zn3—C39iv127.36 (18)
C50—C49—C48120.3 (4)O14'—Zn3—C39iv91.3 (2)
C50—C49—H49119.8O14—Zn3—C39iv105.26 (18)
C48—C49—H49119.8O10iv—Zn3—C39iv29.13 (15)
C49—C50—C51119.4 (4)O12—Zn3—C39iv96.47 (14)
C49—C50—N4119.6 (4)O13—Zn3—C4629.99 (14)
C51—C50—N4121.0 (4)O11iv—Zn3—C46125.23 (17)
C52—C51—C50119.9 (5)N1vi—Zn3—C46101.95 (14)
C52—C51—H51120.0O14'—Zn3—C46137.8 (2)
C50—C51—H51120.0O14—Zn3—C46118.26 (19)
C47—C52—C51121.3 (5)O10iv—Zn3—C4695.02 (14)
C47—C52—H52119.4O12—Zn3—C4628.60 (13)
C51—C52—H52119.4C39iv—Zn3—C46111.76 (16)
N5—C56—C57123.6 (4)
N1—C1—C2—C31.4 (8)C43—C44—C45—C402.1 (8)
C1—C2—C3—C40.4 (8)O12—C46—C47—C522.0 (7)
C1—C2—C3—C6179.1 (5)O13—C46—C47—C52176.4 (4)
C2—C3—C4—C51.0 (8)Zn3—C46—C47—C52163.4 (14)
C6—C3—C4—C5178.5 (5)O12—C46—C47—C48179.5 (4)
C3—C4—C5—N10.1 (10)O13—C46—C47—C482.1 (6)
C4—C3—C6—C7'148.4 (11)Zn3—C46—C47—C4815.1 (18)
C2—C3—C6—C7'32.1 (13)C52—C47—C48—C490.6 (7)
C4—C3—C6—C1028.4 (11)C46—C47—C48—C49179.1 (4)
C2—C3—C6—C10152.1 (9)C47—C48—C49—C500.7 (7)
C4—C3—C6—C7159.9 (8)C48—C49—C50—C512.1 (7)
C2—C3—C6—C719.6 (10)C48—C49—C50—N4179.9 (4)
C4—C3—C6—C10'25.8 (11)C49—C50—C51—C522.3 (8)
C2—C3—C6—C10'153.7 (10)N4—C50—C51—C52179.8 (5)
C7'—C6—C7—C872.0 (14)C48—C47—C52—C510.5 (7)
C10—C6—C7—C89.5 (16)C46—C47—C52—C51179.0 (5)
C10'—C6—C7—C838.4 (14)C50—C51—C52—C471.0 (8)
C3—C6—C7—C8178.3 (9)N5—C56—C57—C580.9 (10)
C6—C7—C8—N21.1 (19)C56—C57—C58—C590.0 (8)
C7'—C6—C10—C945.3 (15)C56—C57—C58—C58ii178.2 (6)
C7—C6—C10—C97.8 (17)C57—C58—C59—C600.4 (8)
C10'—C6—C10—C977.4 (14)C58ii—C58—C59—C60177.8 (6)
C3—C6—C10—C9179.8 (10)C58—C59—C60—N51.8 (9)
N2—C9—C10—C63 (2)Zn3—O14—C61—N6170.5 (3)
C10—C6—C7'—C8'43.7 (18)O14—C61—N6—C630.2 (3)
C7—C6—C7'—C8'84.0 (17)O14—C61—N6—C62179.2 (3)
C10'—C6—C7'—C8'2 (2)Zn1—O1—C64—N7172.6 (6)
C3—C6—C7'—C8'176.4 (13)C65—N7—C64—O1179.94 (19)
C6—C7'—C8'—N212 (3)C66—N7—C64—O10.2 (3)
N2—C9'—C10'—C64 (3)Zn3—O14'—C61'—N6'179.4 (4)
C7'—C6—C10'—C9'8 (2)C63'—N6'—C61'—O14'7.6 (6)
C10—C6—C10'—C9'75.9 (17)C62'—N6'—C61'—O14'172.4 (6)
C7—C6—C10'—C9'37.2 (18)Zn1—O1'—C64'—N7'170.2 (6)
C3—C6—C10'—C9'177.3 (13)C65'—N7'—C64'—O1'172.5 (12)
O3—C11—C12—C178.7 (8)C66'—N7'—C64'—O1'7.5 (12)
O2—C11—C12—C17170.7 (5)C4—C5—N1—C11.8 (9)
O3—C11—C12—C13173.4 (6)C4—C5—N1—Zn3iii176.8 (5)
O2—C11—C12—C137.2 (7)C2—C1—N1—C52.4 (8)
C17—C12—C13—C140.2 (8)C2—C1—N1—Zn3iii176.1 (4)
C11—C12—C13—C14178.1 (5)C7'—C8'—N2—C957 (2)
C12—C13—C14—C151.0 (9)C7'—C8'—N2—C872 (2)
C13—C14—C15—C160.5 (8)C7'—C8'—N2—C9'16 (3)
C13—C14—C15—N3178.9 (5)C7'—C8'—N2—Zn1169.8 (16)
C14—C15—C16—C171.3 (8)C10—C9—N2—C8'51.5 (17)
N3—C15—C16—C17177.0 (5)C10—C9—N2—C811.4 (19)
C15—C16—C17—C122.6 (9)C10—C9—N2—C9'76.3 (16)
C13—C12—C17—C162.0 (8)C10—C9—N2—Zn1177.1 (11)
C11—C12—C17—C16180.0 (5)C7—C8—N2—C8'68.7 (16)
O4—C18—C19—C209.5 (9)C7—C8—N2—C99.0 (17)
O5—C18—C19—C20169.7 (6)C7—C8—N2—C9'41.9 (16)
O4—C18—C19—C24173.0 (6)C7—C8—N2—Zn1178.6 (10)
O5—C18—C19—C247.9 (8)C10'—C9'—N2—C8'8 (2)
C24—C19—C20—C210.5 (10)C10'—C9'—N2—C968.1 (17)
C18—C19—C20—C21178.1 (5)C10'—C9'—N2—C842.7 (19)
C19—C20—C21—C221.0 (10)C10'—C9'—N2—Zn1177.7 (13)
C20—C21—C22—C230.0 (9)C30—C29—N3—C2227.8 (8)
C20—C21—C22—N3177.9 (5)C28—C29—N3—C22152.8 (5)
C21—C22—C23—C241.3 (9)C30—C29—N3—C15144.6 (5)
N3—C22—C23—C24179.2 (6)C28—C29—N3—C1534.8 (8)
C20—C19—C24—C230.8 (10)C21—C22—N3—C2947.7 (8)
C18—C19—C24—C23176.7 (6)C23—C22—N3—C29130.1 (6)
C22—C23—C24—C191.8 (10)C21—C22—N3—C15139.7 (6)
O7—C25—C26—C27166.3 (4)C23—C22—N3—C1542.5 (8)
O6—C25—C26—C2714.3 (6)C14—C15—N3—C29140.7 (5)
O7—C25—C26—C3118.1 (6)C16—C15—N3—C2937.6 (8)
O6—C25—C26—C31161.3 (4)C14—C15—N3—C2246.8 (7)
C31—C26—C27—C281.6 (7)C16—C15—N3—C22134.9 (5)
C25—C26—C27—C28177.3 (5)C37—C36—N4—C4323.0 (7)
C26—C27—C28—C294.2 (8)C35—C36—N4—C43156.2 (5)
C27—C28—C29—C304.0 (8)C37—C36—N4—C50154.9 (5)
C27—C28—C29—N3175.5 (5)C35—C36—N4—C5025.9 (7)
N3—C29—C30—C31178.2 (5)C42—C43—N4—C3647.6 (7)
C28—C29—C30—C311.2 (8)C44—C43—N4—C36135.4 (5)
C29—C30—C31—C261.3 (8)C42—C43—N4—C50134.4 (5)
C27—C26—C31—C301.2 (7)C44—C43—N4—C5042.5 (7)
C25—C26—C31—C30174.7 (4)C49—C50—N4—C36124.9 (5)
O9—C32—C33—C38161.9 (4)C51—C50—N4—C3653.0 (7)
O8—C32—C33—C3816.4 (7)C49—C50—N4—C4357.2 (6)
O9—C32—C33—C3414.6 (6)C51—C50—N4—C43124.9 (5)
O8—C32—C33—C34167.1 (4)C57—C56—N5—C602.2 (9)
C38—C33—C34—C352.4 (7)C57—C56—N5—Zn2177.5 (5)
C32—C33—C34—C35179.1 (5)C59—C60—N5—C562.6 (8)
C33—C34—C35—C364.4 (8)C59—C60—N5—Zn2177.1 (4)
C34—C35—C36—C373.5 (8)O3—C11—O2—Zn11.6 (7)
C34—C35—C36—N4177.2 (5)C12—C11—O2—Zn1177.8 (3)
C35—C36—C37—C380.8 (8)O4—C18—O5—Zn1iv4.8 (7)
N4—C36—C37—C38180.0 (5)C19—C18—O5—Zn1iv174.3 (4)
C36—C37—C38—C331.1 (9)O7—C25—O6—Zn2v4.9 (7)
C34—C33—C38—C370.4 (8)C26—C25—O6—Zn2v174.4 (3)
C32—C33—C38—C37176.3 (5)O6—C25—O7—Zn20.3 (6)
O10—C39—C40—C45173.3 (5)C26—C25—O7—Zn2179.0 (3)
O11—C39—C40—C454.8 (7)O9—C32—O8—Zn2v11.2 (7)
O10—C39—C40—C415.7 (7)C33—C32—O8—Zn2v167.0 (3)
O11—C39—C40—C41176.2 (5)O8—C32—O9—Zn215.4 (6)
C45—C40—C41—C422.2 (7)C33—C32—O9—Zn2162.7 (3)
C39—C40—C41—C42178.8 (4)O11—C39—O10—Zn3i1.7 (5)
C40—C41—C42—C431.7 (7)C40—C39—O10—Zn3i179.7 (4)
C41—C42—C43—C443.7 (7)O10—C39—O11—Zn3i1.9 (5)
C41—C42—C43—N4179.3 (4)C40—C39—O11—Zn3i180.0 (4)
C42—C43—C44—C451.9 (7)O13—C46—O12—Zn31.3 (4)
N4—C43—C44—C45178.9 (4)C47—C46—O12—Zn3177.0 (4)
C41—C40—C45—C444.1 (8)O12—C46—O13—Zn31.6 (5)
C39—C40—C45—C44176.9 (5)C47—C46—O13—Zn3176.8 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y, z+2; (iii) x+1, y+1, z1; (iv) x, y1, z; (v) x+2, y+1, z+2; (vi) x1, y1, z+1.

Experimental details

Crystal data
Chemical formula[Zn3(C21H12NO6)2(C10H8N2)1.5(C3H7NO)2]
Mr1325.21
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)13.6198 (19), 13.962 (2), 26.646 (4)
α, β, γ (°)85.035 (2), 89.776 (2), 86.223 (2)
V3)5037.1 (12)
Z2
Radiation typeMo Kα
µ (mm1)0.75
Crystal size (mm)0.24 × 0.22 × 0.19
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionψ scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.830, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections
39611, 20086, 11697
Rint0.035
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.216, 1.06
No. of reflections20086
No. of parameters859
No. of restraints319
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.04, 1.82

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
N1—Zn3i2.064 (4)O8—Zn2iii2.029 (3)
N2—Zn12.059 (4)O9—Zn22.028 (3)
N5—Zn22.015 (3)O10—Zn3iv2.328 (4)
O2—Zn11.946 (3)O11—Zn3iv2.044 (4)
O5—Zn1ii1.949 (4)O12—Zn32.410 (4)
O6—Zn2iii2.049 (3)O13—Zn32.001 (3)
O7—Zn22.037 (3)Zn2—Zn2iii2.8689 (9)
Symmetry codes: (i) x+1, y+1, z1; (ii) x, y1, z; (iii) x+2, y+1, z+2; (iv) x, y+1, z.
 

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