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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1559–m1560.
Published online 2008 November 20. doi:  10.1107/S160053680803643X
PMCID: PMC2959877

Bis(μ-naphthalene-1,8-dicarboxyl­ato)bis­[aqua­(2,2′-bipyridine)zinc(II)] tetra­hydrate

Abstract

The title complex, [Zn2(C12H6O4)2(C10H8N2)2(H2O)2]·4H2O, is a binuclear complex with two independent ZnII ions in a slightly disorted trigonal bipyramidal environment, coordinated by one aqua ligand, two naphthalene-1,8-dicarboxyl­ate ligands and one 2,2′-bipyridine ligand. π–π Inter­actions [centroid–centroid distance of 3.8489 (5) Å] and O—H(...)O hydrogen bonds connect the mol­ecules, forming a three-dimensional structure.

Related literature

1,8-naphthalene­carboxylic anhydride, which is hydrolysed to the naphthalene-1,8-dicarboxyl­ate ligand under hydro­thermal conditions, is employed as a starting material in the preparation of coordination polymers, see: Feng et al. (2008 [triangle]); He et al. (2007 [triangle]); Wen et al. (2007 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1559-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C12H6O4)2(C10H8N2)2(H2O)2]·4H2O
  • M r = 979.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1559-efi1.jpg
  • a = 10.5774 (12) Å
  • b = 11.3074 (13) Å
  • c = 18.486 (2) Å
  • α = 83.863 (7)°
  • β = 80.254 (7)°
  • γ = 72.197 (6)°
  • V = 2071.2 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.24 mm−1
  • T = 296 (2) K
  • 0.27 × 0.23 × 0.10 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.72, T max = 0.88
  • 34410 measured reflections
  • 9464 independent reflections
  • 6948 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.112
  • S = 1.04
  • 9464 reflections
  • 601 parameters
  • 55 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.75 e Å−3
  • Δρmin = −0.61 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803643X/at2661sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803643X/at2661Isup2.hkl

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

Acknowledgments

The authors thank the Foundation of Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces (grant No. 0506) for supporting this work.

supplementary crystallographic information

Comment

As known, naphthyl-containing aromatic multicarboxylato ligands are versatile building blocks to construct interesting structures with potential properties due to their variety of bridging abilities. In our former work, 1,8-naphthalenecarboxylic anhydride, which is hydrolyzed to naphthalene-1,8-dicarboxylate ligand in hydrothermal condition, is employed as starting material to prepare coordination polymers (Wen et al., 2007; He et al., 2007; Wen et al., 2008; Feng et al., 2008).

The structure of (I) (Fig.1) is a zero-dimensional molecule. Each central ZnII ion is in a slightly distorted trigonal bipyramid environment, coordinated by one aqua ligand, two naphthalene-1,8-dicarboxylate ligands and one 2,2'-bipyridine ligand. Two naphthalene-1,8-dicarboxylate ligands link two five-coordinated ZnII ions to form a eighteen-membered ring. O—H···O hydrogen bonds link independent molecules to form a two-dimensional network. Weak π-π interactions with centroid-centroid distance of 3.849Å connect the layers to yield a three-dimensional structure.

Experimental

Zn(CH3COO)2.2H2O (0.1108 g, 0.5 mmol), 1, 8-naphthalenecarboxylic anhydride (0.0996 g, 0.5 mmol), NaOH (0.0405 g, 1 mmol), 2,2'-bipy (0.0385 g, 0.25 mmol) and H2O-ethanol (2:1, 15 ml) was sealed in a 25 ml stainless-steel reactor with a Teflon liner and was heated at 433 K for 3 d. On completion of the reaction, the reactor was cooled slowly to room temperature and the mixture was filtered, giving pink single crystals suitable for X-ray analysis in yield 39%.

Refinement

The carbon-bound H-atoms were positioned geometrically and included in the refinement using a riding model [C—H 0.93 Å Uiso(H) = 1.2Ueq(C)]. The water H atoms were located from different maps and their positions were refined isotropically, with O—H distances fixed by O—H = 0.85 (2) Å and H···H = 1.30 (2) Å, their displacement parameters were set to 1.5Ueq(O).

Figures

Fig. 1.
View of the title structure, showing 30% probability displacement ellipsoids.
Fig. 2.
The supramolecular structure of the title complex. All H atoms have been omitted for clarity (the green dash lines represent the O—H···O hydrogen bonds and the red lines represent the π-π interactions).

Crystal data

[Zn2(C12H6O4)2(C10H8N2)2(H2O)2]·4H2OZ = 2
Mr = 979.54F000 = 1008
Triclinic, P1Dx = 1.571 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.5774 (12) ÅCell parameters from 7692 reflections
b = 11.3074 (13) Åθ = 1.9–27.6º
c = 18.486 (2) ŵ = 1.24 mm1
α = 83.863 (7)ºT = 296 (2) K
β = 80.254 (7)ºBlock, pink
γ = 72.197 (6)º0.27 × 0.23 × 0.10 mm
V = 2071.2 (4) Å3

Data collection

Bruker APEXII area-detector diffractometer9464 independent reflections
Radiation source: fine-focus sealed tube6948 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 296(2) Kθmax = 27.6º
ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.72, Tmax = 0.88k = −14→14
34410 measured reflectionsl = −24→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112  w = 1/[σ2(Fo2) + (0.0603P)2 + 0.2947P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
9464 reflectionsΔρmax = 0.75 e Å3
601 parametersΔρmin = −0.61 e Å3
55 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
Zn10.19633 (3)0.96571 (3)0.149481 (16)0.03397 (9)
Zn20.20365 (3)0.75742 (3)0.377195 (16)0.03175 (9)
N10.0126 (2)1.0899 (2)0.12294 (12)0.0372 (5)
N20.2418 (2)1.0038 (2)0.03553 (12)0.0365 (5)
N30.1927 (2)0.7166 (2)0.49093 (12)0.0356 (5)
N40.3241 (2)0.56839 (19)0.38523 (12)0.0359 (5)
O10.11681 (17)0.82126 (16)0.16625 (10)0.0368 (4)
O1W0.39543 (18)0.8563 (2)0.15636 (11)0.0428 (5)
H1WA0.386 (3)0.786 (2)0.1646 (18)0.064*
H1WB0.432 (3)0.876 (3)0.1873 (16)0.064*
O20.29945 (19)0.66321 (19)0.17988 (12)0.0497 (5)
O2W0.07124 (18)0.93711 (17)0.38616 (11)0.0387 (4)
H2WA0.005 (2)0.929 (3)0.3695 (17)0.058*
H2WB0.109 (3)0.979 (3)0.3572 (15)0.058*
O3−0.09786 (17)0.88271 (17)0.32078 (11)0.0432 (5)
O3W0.3790 (6)0.3502 (6)−0.0468 (3)0.1672 (18)
H3WA0.437 (8)0.395 (8)−0.041 (5)0.251*
H3WB0.377 (9)0.312 (8)−0.001 (3)0.251*
O40.07943 (16)0.71267 (16)0.31966 (10)0.0350 (4)
O4W0.4334 (3)0.2887 (3)0.0970 (2)0.1181 (13)
H4WA0.43730.31980.13620.177*
H4WB0.37540.25170.11530.177*
O50.2689 (2)1.1513 (2)0.17454 (11)0.0517 (5)
O5W0.5200 (3)0.4728 (3)0.1361 (2)0.1079 (11)
H5WA0.51300.50390.09250.162*
H5WB0.44940.52670.15430.162*
O60.17171 (17)1.03172 (16)0.25133 (10)0.0373 (4)
O6W0.6463 (2)1.0749 (2)0.30347 (15)0.0595 (6)
H6WA0.587 (3)1.046 (3)0.296 (2)0.089*
H6WB0.721 (2)1.019 (3)0.301 (2)0.089*
O70.46117 (17)0.94964 (17)0.27237 (10)0.0390 (4)
O80.36064 (17)0.81452 (16)0.33168 (11)0.0402 (4)
C10.1562 (3)0.5342 (3)0.11411 (17)0.0490 (7)
H1A0.24440.52470.09240.059*
C20.0848 (4)0.4619 (3)0.0920 (2)0.0635 (9)
H2A0.12620.40370.05690.076*
C3−0.0445 (4)0.4768 (3)0.1220 (2)0.0606 (9)
H3A−0.09230.43070.10560.073*
C4−0.1081 (3)0.5600 (3)0.17708 (17)0.0439 (7)
C5−0.2442 (3)0.5775 (3)0.2066 (2)0.0528 (8)
H5A−0.29140.53150.18950.063*
C6−0.3076 (3)0.6585 (3)0.25848 (19)0.0494 (8)
H6A−0.39820.67050.27570.059*
C7−0.2357 (3)0.7248 (3)0.28642 (17)0.0417 (7)
H7A−0.27930.77960.32310.050*
C8−0.1022 (2)0.7105 (2)0.26084 (15)0.0344 (6)
C9−0.0344 (3)0.6310 (2)0.20291 (15)0.0348 (6)
C100.0992 (3)0.6185 (2)0.16696 (15)0.0359 (6)
C110.1776 (2)0.7069 (2)0.17370 (14)0.0352 (6)
C12−0.0337 (2)0.7753 (2)0.30211 (14)0.0328 (5)
C130.3600 (3)0.9583 (3)−0.00541 (16)0.0458 (7)
H13A0.42860.90140.01660.055*
C140.3852 (3)0.9922 (3)−0.07931 (18)0.0550 (8)
H14A0.46920.9592−0.10640.066*
C150.2843 (3)1.0749 (3)−0.11157 (18)0.0608 (9)
H15A0.29891.0995−0.16110.073*
C160.1611 (3)1.1218 (3)−0.07067 (17)0.0557 (8)
H16A0.09131.1777−0.09230.067*
C170.1416 (3)1.0849 (2)0.00341 (15)0.0374 (6)
C180.0132 (3)1.1297 (2)0.05200 (15)0.0360 (6)
C19−0.1027 (3)1.2065 (3)0.02682 (18)0.0493 (7)
H19A−0.10171.2335−0.02250.059*
C20−0.2188 (3)1.2422 (3)0.0757 (2)0.0560 (8)
H20A−0.29711.29380.05960.067*
C21−0.2186 (3)1.2014 (3)0.1479 (2)0.0559 (8)
H21A−0.29641.22500.18170.067*
C22−0.1012 (3)1.1249 (3)0.16987 (17)0.0478 (7)
H22A−0.10111.09670.21900.057*
C230.1569 (3)1.3201 (3)0.29420 (18)0.0451 (7)
H23A0.14221.35690.24770.054*
C240.1184 (3)1.3945 (3)0.3548 (2)0.0530 (8)
H24A0.07941.47990.34850.064*
C250.1385 (3)1.3411 (3)0.42265 (19)0.0495 (7)
H25A0.10721.38960.46320.059*
C260.2062 (3)1.2129 (3)0.43301 (16)0.0409 (6)
C270.2336 (3)1.1603 (3)0.50399 (17)0.0509 (8)
H27A0.20451.21040.54390.061*
C280.3013 (3)1.0385 (3)0.51466 (17)0.0536 (8)
H28A0.31781.00520.56150.064*
C290.3461 (3)0.9633 (3)0.45468 (16)0.0452 (7)
H29A0.39360.88000.46230.054*
C300.3222 (2)1.0086 (2)0.38493 (14)0.0335 (6)
C310.2498 (2)1.1365 (2)0.37202 (14)0.0322 (5)
C320.2158 (2)1.1942 (2)0.30217 (15)0.0353 (6)
C330.2235 (3)1.1223 (2)0.23787 (15)0.0367 (6)
C340.3838 (2)0.9198 (2)0.32488 (15)0.0335 (6)
C350.1273 (3)0.7988 (3)0.54229 (16)0.0432 (7)
H35A0.07980.87870.52700.052*
C360.1279 (3)0.7698 (3)0.61537 (17)0.0483 (7)
H36A0.08390.82950.64920.058*
C370.1941 (3)0.6512 (3)0.63862 (17)0.0562 (8)
H37A0.19390.62910.68850.067*
C380.2604 (3)0.5660 (3)0.58776 (17)0.0495 (7)
H38A0.30550.48510.60280.059*
C390.2603 (2)0.6008 (2)0.51321 (15)0.0348 (6)
C400.3340 (2)0.5173 (2)0.45381 (15)0.0340 (6)
C410.4099 (3)0.3947 (3)0.46601 (18)0.0464 (7)
H41A0.41750.36090.51380.056*
C420.4735 (3)0.3240 (3)0.40738 (19)0.0521 (8)
H42A0.52390.24160.41490.062*
C430.4618 (3)0.3763 (3)0.33749 (19)0.0515 (8)
H43A0.50380.33000.29680.062*
C440.3867 (3)0.4988 (3)0.32860 (17)0.0459 (7)
H44A0.37950.53440.28120.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.03452 (16)0.03960 (18)0.02821 (17)−0.01121 (13)−0.00770 (12)0.00229 (13)
Zn20.03274 (16)0.02909 (16)0.03286 (18)−0.00729 (12)−0.00830 (12)0.00109 (12)
N10.0382 (12)0.0408 (13)0.0336 (12)−0.0122 (10)−0.0093 (10)0.0020 (10)
N20.0388 (12)0.0432 (13)0.0303 (12)−0.0155 (10)−0.0079 (10)0.0010 (10)
N30.0353 (11)0.0327 (12)0.0380 (13)−0.0085 (9)−0.0080 (10)0.0016 (10)
N40.0381 (11)0.0299 (11)0.0391 (13)−0.0065 (9)−0.0109 (10)−0.0009 (10)
O10.0363 (9)0.0335 (10)0.0412 (11)−0.0107 (8)−0.0095 (8)0.0030 (8)
O1W0.0355 (8)0.0534 (13)0.0393 (11)−0.0132 (8)−0.0079 (8)0.0024 (10)
O20.0385 (10)0.0480 (12)0.0596 (14)−0.0069 (9)−0.0121 (10)0.0004 (10)
O2W0.0365 (10)0.0325 (10)0.0477 (12)−0.0085 (8)−0.0102 (9)−0.0033 (9)
O30.0361 (10)0.0396 (11)0.0524 (12)−0.0026 (8)−0.0126 (9)−0.0116 (9)
O3W0.183 (5)0.195 (5)0.125 (4)−0.062 (4)−0.011 (4)−0.009 (3)
O40.0342 (9)0.0324 (9)0.0385 (10)−0.0048 (7)−0.0145 (8)−0.0022 (8)
O4W0.084 (2)0.083 (2)0.173 (4)−0.0234 (17)0.019 (2)−0.006 (2)
O50.0615 (13)0.0598 (13)0.0341 (12)−0.0205 (11)−0.0081 (10)0.0063 (10)
O5W0.0714 (18)0.102 (2)0.136 (3)0.0045 (17)−0.0108 (19)−0.041 (2)
O60.0417 (10)0.0381 (10)0.0366 (10)−0.0146 (8)−0.0137 (8)−0.0001 (8)
O6W0.0530 (13)0.0523 (14)0.0749 (16)−0.0155 (10)−0.0125 (13)−0.0058 (12)
O70.0333 (9)0.0439 (11)0.0408 (11)−0.0142 (8)−0.0051 (8)0.0013 (9)
O80.0349 (9)0.0324 (10)0.0516 (12)−0.0097 (8)−0.0023 (8)−0.0014 (9)
C10.0535 (17)0.0436 (17)0.0477 (18)−0.0086 (14)−0.0102 (15)−0.0045 (14)
C20.087 (3)0.049 (2)0.058 (2)−0.0159 (18)−0.0169 (19)−0.0201 (17)
C30.078 (2)0.053 (2)0.063 (2)−0.0280 (17)−0.0266 (19)−0.0073 (17)
C40.0553 (17)0.0394 (16)0.0446 (17)−0.0183 (13)−0.0231 (14)0.0034 (13)
C50.0549 (18)0.0497 (18)0.067 (2)−0.0287 (15)−0.0309 (17)0.0120 (17)
C60.0389 (15)0.0492 (18)0.064 (2)−0.0175 (13)−0.0170 (15)0.0111 (16)
C70.0363 (14)0.0406 (15)0.0477 (17)−0.0095 (12)−0.0132 (13)0.0060 (13)
C80.0362 (13)0.0333 (14)0.0352 (15)−0.0103 (11)−0.0141 (11)0.0061 (11)
C90.0409 (14)0.0305 (13)0.0363 (15)−0.0109 (11)−0.0178 (12)0.0045 (11)
C100.0426 (14)0.0284 (13)0.0349 (15)−0.0052 (11)−0.0125 (12)0.0017 (11)
C110.0346 (13)0.0407 (15)0.0281 (14)−0.0077 (11)−0.0056 (11)−0.0011 (11)
C120.0340 (13)0.0354 (14)0.0299 (14)−0.0127 (11)−0.0045 (11)0.0010 (11)
C130.0402 (15)0.0597 (19)0.0399 (17)−0.0185 (13)−0.0049 (13)−0.0036 (14)
C140.0535 (18)0.069 (2)0.0431 (18)−0.0258 (16)0.0070 (15)−0.0055 (16)
C150.068 (2)0.079 (2)0.0332 (17)−0.0253 (19)−0.0030 (16)0.0110 (16)
C160.061 (2)0.068 (2)0.0358 (17)−0.0178 (17)−0.0149 (15)0.0126 (16)
C170.0471 (15)0.0385 (15)0.0319 (14)−0.0182 (12)−0.0127 (12)0.0025 (12)
C180.0410 (14)0.0347 (14)0.0355 (15)−0.0135 (11)−0.0132 (12)0.0037 (11)
C190.0533 (18)0.0475 (17)0.0455 (18)−0.0095 (14)−0.0184 (15)0.0060 (14)
C200.0463 (17)0.0517 (19)0.067 (2)−0.0051 (14)−0.0224 (17)0.0040 (17)
C210.0388 (16)0.060 (2)0.063 (2)−0.0062 (14)−0.0051 (15)−0.0041 (17)
C220.0438 (16)0.0539 (18)0.0427 (17)−0.0121 (13)−0.0059 (13)0.0027 (14)
C230.0510 (16)0.0367 (15)0.0507 (18)−0.0151 (13)−0.0160 (14)0.0046 (13)
C240.0558 (18)0.0318 (15)0.075 (2)−0.0122 (13)−0.0204 (17)−0.0036 (15)
C250.0515 (17)0.0433 (17)0.058 (2)−0.0157 (14)−0.0076 (15)−0.0181 (15)
C260.0410 (14)0.0456 (16)0.0425 (17)−0.0202 (12)−0.0081 (12)−0.0044 (13)
C270.0605 (19)0.062 (2)0.0379 (17)−0.0275 (16)−0.0056 (14)−0.0110 (15)
C280.068 (2)0.064 (2)0.0357 (17)−0.0280 (17)−0.0161 (15)0.0076 (15)
C290.0516 (16)0.0448 (17)0.0425 (17)−0.0170 (13)−0.0156 (14)0.0061 (14)
C300.0326 (12)0.0371 (14)0.0352 (15)−0.0163 (11)−0.0073 (11)0.0010 (11)
C310.0329 (12)0.0343 (14)0.0335 (14)−0.0151 (10)−0.0073 (11)−0.0006 (11)
C320.0371 (13)0.0340 (14)0.0383 (15)−0.0148 (11)−0.0083 (11)0.0009 (12)
C330.0376 (13)0.0361 (14)0.0354 (15)−0.0072 (11)−0.0136 (12)0.0052 (12)
C340.0262 (12)0.0358 (14)0.0391 (15)−0.0074 (10)−0.0132 (11)0.0034 (12)
C350.0416 (15)0.0417 (16)0.0438 (17)−0.0087 (12)−0.0062 (13)−0.0017 (13)
C360.0503 (17)0.0539 (19)0.0360 (17)−0.0089 (14)−0.0029 (13)−0.0069 (14)
C370.065 (2)0.068 (2)0.0299 (16)−0.0133 (17)−0.0075 (15)0.0041 (15)
C380.0579 (18)0.0446 (17)0.0416 (18)−0.0085 (14)−0.0150 (15)0.0093 (14)
C390.0315 (12)0.0370 (14)0.0385 (15)−0.0130 (11)−0.0102 (11)0.0040 (12)
C400.0328 (13)0.0324 (13)0.0403 (15)−0.0124 (10)−0.0115 (11)0.0013 (11)
C410.0460 (16)0.0370 (15)0.0537 (19)−0.0062 (12)−0.0168 (14)0.0053 (14)
C420.0492 (17)0.0354 (16)0.067 (2)−0.0026 (13)−0.0163 (16)−0.0010 (15)
C430.0493 (17)0.0425 (17)0.056 (2)−0.0018 (13)−0.0061 (15)−0.0129 (15)
C440.0525 (17)0.0423 (16)0.0398 (17)−0.0086 (13)−0.0077 (14)−0.0027 (13)

Geometric parameters (Å, °)

Zn1—O12.0285 (17)C9—C101.428 (4)
Zn1—O62.0458 (19)C10—C111.506 (4)
Zn1—N22.108 (2)C13—C141.382 (4)
Zn1—O1W2.1085 (19)C13—H13A0.9300
Zn1—N12.121 (2)C14—C151.363 (5)
Zn2—O81.9871 (17)C14—H14A0.9300
Zn2—O42.0270 (17)C15—C161.371 (5)
Zn2—O2W2.0906 (19)C15—H15A0.9300
Zn2—N32.095 (2)C16—C171.388 (4)
Zn2—N42.132 (2)C16—H16A0.9300
N1—C221.337 (4)C17—C181.474 (4)
N1—C181.340 (3)C18—C191.389 (4)
N2—C131.330 (4)C19—C201.373 (5)
N2—C171.349 (3)C19—H19A0.9300
N3—C391.344 (3)C20—C211.366 (5)
N3—C351.348 (4)C20—H20A0.9300
N4—C441.333 (4)C21—C221.376 (4)
N4—C401.343 (3)C21—H21A0.9300
O1—C111.261 (3)C22—H22A0.9300
O1W—H1WA0.824 (17)C23—C321.372 (4)
O1W—H1WB0.825 (17)C23—C241.403 (4)
O2—C111.251 (3)C23—H23A0.9300
O2W—H2WA0.848 (17)C24—C251.353 (5)
O2W—H2WB0.808 (17)C24—H24A0.9300
O3—C121.249 (3)C25—C261.416 (4)
O3W—H3WA0.93 (9)C25—H25A0.9300
O3W—H3WB0.91 (6)C26—C271.420 (4)
O4—C121.266 (3)C26—C311.421 (4)
O4W—H4WA0.8502C27—C281.354 (5)
O4W—H4WB0.8504C27—H27A0.9300
O5—C331.238 (3)C28—C291.398 (4)
O5W—H5WA0.8503C28—H28A0.9300
O5W—H5WB0.8499C29—C301.371 (4)
O6—C331.286 (3)C29—H29A0.9300
O6W—H6WA0.829 (18)C30—C311.430 (3)
O6W—H6WB0.849 (18)C30—C341.503 (4)
O7—C341.247 (3)C31—C321.434 (4)
O8—C341.276 (3)C32—C331.488 (4)
C1—C101.370 (4)C35—C361.357 (4)
C1—C21.399 (4)C35—H35A0.9300
C1—H1A0.9300C36—C371.370 (4)
C2—C31.353 (5)C36—H36A0.9300
C2—H2A0.9300C37—C381.365 (4)
C3—C41.401 (5)C37—H37A0.9300
C3—H3A0.9300C38—C391.392 (4)
C4—C51.411 (4)C38—H38A0.9300
C4—C91.440 (4)C39—C401.479 (4)
C5—C61.343 (5)C40—C411.390 (4)
C5—H5A0.9300C41—C421.370 (4)
C6—C71.404 (4)C41—H41A0.9300
C6—H6A0.9300C42—C431.371 (4)
C7—C81.376 (4)C42—H42A0.9300
C7—H7A0.9300C43—C441.378 (4)
C8—C91.422 (4)C43—H43A0.9300
C8—C121.508 (4)C44—H44A0.9300
O1—Zn1—O6104.86 (7)C14—C15—H15A120.1
O1—Zn1—N2109.17 (8)C16—C15—H15A120.1
O6—Zn1—N2144.94 (8)C15—C16—C17119.3 (3)
O1—Zn1—O1W95.57 (7)C15—C16—H16A120.4
O6—Zn1—O1W93.01 (8)C17—C16—H16A120.4
N2—Zn1—O1W91.91 (8)N2—C17—C16121.0 (3)
O1—Zn1—N191.35 (8)N2—C17—C18115.6 (2)
O6—Zn1—N193.69 (8)C16—C17—C18123.4 (3)
N2—Zn1—N177.50 (8)N1—C18—C19120.8 (3)
O1W—Zn1—N1168.82 (8)N1—C18—C17116.1 (2)
O8—Zn2—O4124.30 (8)C19—C18—C17123.0 (3)
O8—Zn2—O2W94.47 (7)C20—C19—C18119.2 (3)
O4—Zn2—O2W89.84 (7)C20—C19—H19A120.4
O8—Zn2—N3114.43 (8)C18—C19—H19A120.4
O4—Zn2—N3120.50 (8)C21—C20—C19119.6 (3)
O2W—Zn2—N394.63 (8)C21—C20—H20A120.2
O8—Zn2—N492.17 (8)C19—C20—H20A120.2
O4—Zn2—N491.54 (8)C20—C21—C22118.8 (3)
O2W—Zn2—N4170.91 (8)C20—C21—H21A120.6
N3—Zn2—N476.94 (9)C22—C21—H21A120.6
C22—N1—C18119.3 (2)N1—C22—C21122.2 (3)
C22—N1—Zn1125.40 (19)N1—C22—H22A118.9
C18—N1—Zn1115.17 (18)C21—C22—H22A118.9
C13—N2—C17118.7 (2)C32—C23—C24121.3 (3)
C13—N2—Zn1125.72 (19)C32—C23—H23A119.4
C17—N2—Zn1115.56 (18)C24—C23—H23A119.4
C39—N3—C35118.5 (2)C25—C24—C23119.5 (3)
C39—N3—Zn2116.67 (18)C25—C24—H24A120.2
C35—N3—Zn2124.75 (18)C23—C24—H24A120.2
C44—N4—C40118.9 (2)C24—C25—C26121.2 (3)
C44—N4—Zn2125.46 (19)C24—C25—H25A119.4
C40—N4—Zn2115.66 (18)C26—C25—H25A119.4
C11—O1—Zn1127.96 (16)C25—C26—C27120.3 (3)
Zn1—O1W—H1WA102 (2)C25—C26—C31120.1 (3)
Zn1—O1W—H1WB116 (2)C27—C26—C31119.6 (3)
H1WA—O1W—H1WB113 (3)C28—C27—C26121.2 (3)
Zn2—O2W—H2WA101 (2)C28—C27—H27A119.4
Zn2—O2W—H2WB103 (2)C26—C27—H27A119.4
H2WA—O2W—H2WB110 (2)C27—C28—C29119.5 (3)
H3WA—O3W—H3WB97 (8)C27—C28—H28A120.2
C12—O4—Zn2131.02 (16)C29—C28—H28A120.2
H4WA—O4W—H4WB97.3C30—C29—C28121.9 (3)
H5WA—O5W—H5WB93.0C30—C29—H29A119.0
C33—O6—Zn1102.49 (16)C28—C29—H29A119.0
H6WA—O6W—H6WB110 (3)C29—C30—C31119.9 (3)
C34—O8—Zn2133.57 (17)C29—C30—C34116.3 (2)
C10—C1—C2121.6 (3)C31—C30—C34123.7 (2)
C10—C1—H1A119.2C26—C31—C30117.9 (2)
C2—C1—H1A119.2C26—C31—C32116.9 (2)
C3—C2—C1119.8 (3)C30—C31—C32125.1 (2)
C3—C2—H2A120.1C23—C32—C31120.6 (3)
C1—C2—H2A120.1C23—C32—C33115.7 (2)
C2—C3—C4121.5 (3)C31—C32—C33123.1 (2)
C2—C3—H3A119.2O5—C33—O6121.4 (3)
C4—C3—H3A119.2O5—C33—C32122.9 (2)
C3—C4—C5121.1 (3)O6—C33—C32115.6 (2)
C3—C4—C9119.5 (3)O7—C34—O8122.8 (3)
C5—C4—C9119.4 (3)O7—C34—C30118.4 (2)
C6—C5—C4122.0 (3)O8—C34—C30118.7 (2)
C6—C5—H5A119.0N3—C35—C36122.7 (3)
C4—C5—H5A119.0N3—C35—H35A118.6
C5—C6—C7119.3 (3)C36—C35—H35A118.6
C5—C6—H6A120.3C35—C36—C37119.1 (3)
C7—C6—H6A120.3C35—C36—H36A120.4
C8—C7—C6121.5 (3)C37—C36—H36A120.4
C8—C7—H7A119.2C38—C37—C36119.3 (3)
C6—C7—H7A119.2C38—C37—H37A120.3
C7—C8—C9120.4 (2)C36—C37—H37A120.3
C7—C8—C12115.7 (3)C37—C38—C39119.6 (3)
C9—C8—C12123.7 (2)C37—C38—H38A120.2
C8—C9—C10125.4 (2)C39—C38—H38A120.2
C8—C9—C4117.1 (2)N3—C39—C38120.7 (3)
C10—C9—C4117.4 (3)N3—C39—C40115.5 (2)
C1—C10—C9120.0 (3)C38—C39—C40123.8 (2)
C1—C10—C11115.1 (2)N4—C40—C41120.9 (3)
C9—C10—C11124.2 (2)N4—C40—C39115.2 (2)
O2—C11—O1124.6 (2)C41—C40—C39123.9 (3)
O2—C11—C10118.8 (2)C42—C41—C40119.7 (3)
O1—C11—C10116.3 (2)C42—C41—H41A120.2
O3—C12—O4125.6 (2)C40—C41—H41A120.2
O3—C12—C8117.1 (2)C41—C42—C43119.1 (3)
O4—C12—C8117.1 (2)C41—C42—H42A120.5
N2—C13—C14122.8 (3)C43—C42—H42A120.5
N2—C13—H13A118.6C42—C43—C44118.8 (3)
C14—C13—H13A118.6C42—C43—H43A120.6
C15—C14—C13118.5 (3)C44—C43—H43A120.6
C15—C14—H14A120.8N4—C44—C43122.7 (3)
C13—C14—H14A120.8N4—C44—H44A118.7
C14—C15—C16119.8 (3)C43—C44—H44A118.7
O1—Zn1—N1—C2267.5 (2)C13—C14—C15—C16−0.4 (5)
O6—Zn1—N1—C22−37.5 (2)C14—C15—C16—C170.7 (5)
N2—Zn1—N1—C22176.9 (2)C13—N2—C17—C16−0.7 (4)
O1W—Zn1—N1—C22−164.2 (4)Zn1—N2—C17—C16177.1 (2)
O1—Zn1—N1—C18−109.18 (19)C13—N2—C17—C18179.1 (2)
O6—Zn1—N1—C18145.83 (18)Zn1—N2—C17—C18−3.1 (3)
N2—Zn1—N1—C180.16 (18)C15—C16—C17—N2−0.1 (5)
O1W—Zn1—N1—C1819.1 (5)C15—C16—C17—C18−180.0 (3)
O1—Zn1—N2—C13−93.7 (2)C22—N1—C18—C19−0.1 (4)
O6—Zn1—N2—C13100.9 (2)Zn1—N1—C18—C19176.8 (2)
O1W—Zn1—N2—C132.9 (2)C22—N1—C18—C17−178.7 (2)
N1—Zn1—N2—C13179.3 (2)Zn1—N1—C18—C17−1.8 (3)
O1—Zn1—N2—C1788.69 (19)N2—C17—C18—N13.3 (3)
O6—Zn1—N2—C17−76.8 (2)C16—C17—C18—N1−176.9 (3)
O1W—Zn1—N2—C17−174.74 (18)N2—C17—C18—C19−175.3 (3)
N1—Zn1—N2—C171.65 (18)C16—C17—C18—C194.5 (4)
O8—Zn2—N3—C39−86.63 (18)N1—C18—C19—C200.3 (4)
O4—Zn2—N3—C3983.77 (18)C17—C18—C19—C20178.8 (3)
O2W—Zn2—N3—C39176.33 (17)C18—C19—C20—C21−0.2 (5)
N4—Zn2—N3—C39−0.22 (16)C19—C20—C21—C22−0.2 (5)
O8—Zn2—N3—C3591.0 (2)C18—N1—C22—C21−0.3 (4)
O4—Zn2—N3—C35−98.6 (2)Zn1—N1—C22—C21−176.8 (2)
O2W—Zn2—N3—C35−6.1 (2)C20—C21—C22—N10.4 (5)
N4—Zn2—N3—C35177.4 (2)C32—C23—C24—C25−0.7 (4)
O8—Zn2—N4—C44−66.1 (2)C23—C24—C25—C264.5 (4)
O4—Zn2—N4—C4458.3 (2)C24—C25—C26—C27176.1 (3)
N3—Zn2—N4—C44179.3 (2)C24—C25—C26—C31−2.6 (4)
O8—Zn2—N4—C40114.95 (18)C25—C26—C27—C28−178.3 (3)
O4—Zn2—N4—C40−120.64 (17)C31—C26—C27—C280.4 (4)
N3—Zn2—N4—C400.36 (17)C26—C27—C28—C290.6 (5)
O6—Zn1—O1—C11−97.8 (2)C27—C28—C29—C30−0.9 (5)
N2—Zn1—O1—C1190.8 (2)C28—C29—C30—C310.3 (4)
O1W—Zn1—O1—C11−3.2 (2)C28—C29—C30—C34176.1 (2)
N1—Zn1—O1—C11168.0 (2)C25—C26—C31—C30177.7 (2)
O8—Zn2—O4—C12−97.7 (2)C27—C26—C31—C30−0.9 (3)
O2W—Zn2—O4—C12−2.4 (2)C25—C26—C31—C32−3.1 (3)
N3—Zn2—O4—C1292.9 (2)C27—C26—C31—C32178.3 (2)
N4—Zn2—O4—C12168.6 (2)C29—C30—C31—C260.6 (3)
O1—Zn1—O6—C33179.91 (15)C34—C30—C31—C26−174.9 (2)
N2—Zn1—O6—C33−14.3 (2)C29—C30—C31—C32−178.5 (2)
O1W—Zn1—O6—C3383.34 (16)C34—C30—C31—C326.0 (4)
N1—Zn1—O6—C33−87.71 (16)C24—C23—C32—C31−5.2 (4)
O4—Zn2—O8—C34106.8 (2)C24—C23—C32—C33166.7 (3)
O2W—Zn2—O8—C3413.9 (2)C26—C31—C32—C236.9 (3)
N3—Zn2—O8—C34−83.2 (2)C30—C31—C32—C23−174.0 (2)
N4—Zn2—O8—C34−159.9 (2)C26—C31—C32—C33−164.3 (2)
C10—C1—C2—C31.5 (5)C30—C31—C32—C3314.8 (4)
C1—C2—C3—C4−2.5 (5)Zn1—O6—C33—O51.8 (3)
C2—C3—C4—C5178.2 (3)Zn1—O6—C33—C32177.63 (17)
C2—C3—C4—C9−0.3 (5)C23—C32—C33—O550.6 (4)
C3—C4—C5—C6−178.8 (3)C31—C32—C33—O5−137.8 (3)
C9—C4—C5—C6−0.2 (4)C23—C32—C33—O6−125.2 (3)
C4—C5—C6—C7−2.4 (5)C31—C32—C33—O646.4 (3)
C5—C6—C7—C81.3 (4)Zn2—O8—C34—O7−150.56 (19)
C6—C7—C8—C92.4 (4)Zn2—O8—C34—C3033.3 (3)
C6—C7—C8—C12−172.8 (2)C29—C30—C34—O7−122.4 (3)
C7—C8—C9—C10173.3 (2)C31—C30—C34—O753.3 (3)
C12—C8—C9—C10−11.9 (4)C29—C30—C34—O853.9 (3)
C7—C8—C9—C4−4.8 (4)C31—C30—C34—O8−130.5 (2)
C12—C8—C9—C4170.0 (2)C39—N3—C35—C360.6 (4)
C3—C4—C9—C8−177.6 (3)Zn2—N3—C35—C36−177.0 (2)
C5—C4—C9—C83.8 (4)N3—C35—C36—C37−2.0 (5)
C3—C4—C9—C104.1 (4)C35—C36—C37—C381.5 (5)
C5—C4—C9—C10−174.5 (2)C36—C37—C38—C390.3 (5)
C2—C1—C10—C92.4 (4)C35—N3—C39—C381.2 (4)
C2—C1—C10—C11−168.1 (3)Zn2—N3—C39—C38179.0 (2)
C8—C9—C10—C1176.8 (3)C35—N3—C39—C40−177.7 (2)
C4—C9—C10—C1−5.0 (4)Zn2—N3—C39—C400.1 (3)
C8—C9—C10—C11−13.7 (4)C37—C38—C39—N3−1.7 (4)
C4—C9—C10—C11164.5 (2)C37—C38—C39—C40177.2 (3)
Zn1—O1—C11—O28.2 (4)C44—N4—C40—C411.1 (4)
Zn1—O1—C11—C10−165.51 (17)Zn2—N4—C40—C41−179.89 (19)
C1—C10—C11—O2−51.0 (3)C44—N4—C40—C39−179.4 (2)
C9—C10—C11—O2139.0 (3)Zn2—N4—C40—C39−0.4 (3)
C1—C10—C11—O1123.1 (3)N3—C39—C40—N40.2 (3)
C9—C10—C11—O1−46.9 (4)C38—C39—C40—N4−178.7 (2)
Zn2—O4—C12—O3−3.4 (4)N3—C39—C40—C41179.7 (2)
Zn2—O4—C12—C8−177.67 (16)C38—C39—C40—C410.8 (4)
C7—C8—C12—O3−41.7 (3)N4—C40—C41—C42−1.3 (4)
C9—C8—C12—O3143.2 (3)C39—C40—C41—C42179.3 (3)
C7—C8—C12—O4133.0 (3)C40—C41—C42—C430.6 (4)
C9—C8—C12—O4−42.0 (3)C41—C42—C43—C440.3 (5)
C17—N2—C13—C141.0 (4)C40—N4—C44—C43−0.2 (4)
Zn1—N2—C13—C14−176.5 (2)Zn2—N4—C44—C43−179.1 (2)
N2—C13—C14—C15−0.5 (5)C42—C43—C44—N4−0.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O20.824 (17)1.861 (19)2.644 (3)158 (3)
O1W—H1WB···O70.825 (17)1.97 (2)2.763 (3)162 (3)
O2W—H2WA···O30.848 (17)1.743 (19)2.570 (3)164 (3)
O2W—H2WB···O60.808 (17)2.05 (2)2.778 (3)150 (3)
O3W—H3WA···O5Wi0.93 (9)2.26 (7)2.807 (7)117 (6)
O3W—H3WB···O4W0.91 (6)1.97 (5)2.785 (6)149 (7)
O4W—H4WA···O5W0.852.162.721 (5)123
O4W—H4WB···O5ii0.851.962.798 (4)167
O5W—H5WA···O3Wi0.852.302.807 (7)119
O5W—H5WB···O20.851.882.719 (3)170
O6W—H6WA···O70.829 (18)2.08 (2)2.902 (3)171 (4)
O6W—H6WB···O3iii0.849 (18)2.117 (19)2.949 (3)167 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2661).

References

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