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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m697.
Published online 2008 April 23. doi:  10.1107/S1600536808010271
PMCID: PMC2961073

Bis(μ-2,2′-oxydibenzoato-κ4 O,O′:O′′,O′′′)bis­[(4,4′-dimethyl-2,2′-bipyridine-κ2 N,N′)zinc(II)] dihydrate

Abstract

In the title compound, [Zn2(C14H8O5)2(C12H12N2)2]·2H2O, the ZnII atom exhibits a distorted octa­hedral coordination geometry, defined by two N atoms from one 4,4′-dimethyl-2,2′-bipyridine ligand and four O atoms from two bridging 2,2′-oxydibenzoate ligands. The mol­ecule is a centrosymmetric dimer. π–π Stacking inter­actions are observed between the 4,4′-dimethyl-2,2′-bipyridine ligands, with a centroid–centroid distance of 3.649 (2) Å.

Related literature

For related literature, see: Allen et al. (1987 [triangle]); Zhang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m697-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C14H8O5)2(C12H12N2)2]·2H2O
  • M r = 1047.65
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m697-efi1.jpg
  • a = 10.425 (2) Å
  • b = 10.866 (2) Å
  • c = 11.960 (2) Å
  • α = 68.413 (4)°
  • β = 66.721 (3)°
  • γ = 78.348 (4)°
  • V = 1154.7 (4) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.11 mm−1
  • T = 293 (2) K
  • 0.20 × 0.16 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.808, T max = 0.851
  • 6797 measured reflections
  • 4484 independent reflections
  • 3788 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.123
  • S = 1.16
  • 4484 reflections
  • 318 parameters
  • H-atom parameters constrained
  • Δρmax = 0.79 e Å−3
  • Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010271/hy2127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010271/hy2127Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support provided by the Henan Administration of Science and Technology (grant No. 0111030700).

supplementary crystallographic information

Comment

As part of our ongoing studies (Zhang et al., 2008), we synthesized the title compound and report here its crystal structure.

The bond lengths and angles of the title compound are within normal ranges (Allen et al., 1987) (Table 1). Intermolecular hydrogen bonds are formed between the water molecule and the carboxylate groups (Fig. 1; Table 2). The molecule is centrosymmetric with an inversion center located at the midpoint of the Zn1 and Zn1i atoms [symmetry code (i): 1 - x, 2 - y, 1 - z]. The asymmetric unit thus contains one-half molecule. The ZnII atom exhibits a distorted octahedral coordination geometry, defined by two N atoms from one 4,4'-dimethyl-2,2'-bipyridine (dbpy) ligand and four O atoms from two 2,2'-oxydibenzoate (odb) ligands. The two carboxylate groups of each odb ligand coordinate to two different Zn atoms.

The π–π stacking interactions between the aromatic rings of the dbpy ligands are observed, with a centroid–centroid distance of 3.649 (2)Å [Fig. 2; Cg1 = the centroid of N1ii, C15ii, C16ii, C17ii, C19ii, C20ii and Cg2 = the centroid of N2, C21, C22, C23, C25, C26; symmetry code: (ii) 2 - x, 2 - y, 1 - z].

Experimental

The title compound was synthesized hydrothermally in a Teflon-lined autoclave (23 ml) by heating a mixture of H2odb (0.052 g, 0.2 mmol), dbpy (0.037 g, 0.2 mmol), Zn(NO3)2.6H2O (0.059 g, 0.2 mmol) and one drop of Et3N (pH = 8~9) in water (10 ml) at 393 K for 3 d. Colorless single crystals were collected in 56% yield based on Zn.

Refinement

H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (methyl) Å and with Uiso(H) = 1.2(1.5 for methyl groups)Ueq(C). The H atoms of the water molecule were located from a difference Fourier map and fixed in the final refinements with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 20% probability level. Hydrogen bonds are indicated by dashed lines. [Symmetry code (i): 1 - x, 2 - y, 1 - z.]
Fig. 2.
A view of the crystal packing, showing the π–π stacking interaction.

Crystal data

[Zn2(C14H8O5)2(C12H12N2)2]·2H2OZ = 1
Mr = 1047.65F000 = 540
Triclinic, P1Dx = 1.507 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.425 (2) ÅCell parameters from 2731 reflections
b = 10.866 (2) Åθ = 2.3–27.8º
c = 11.960 (2) ŵ = 1.11 mm1
α = 68.413 (4)ºT = 293 (2) K
β = 66.721 (3)ºBlock, colorless
γ = 78.348 (4)º0.20 × 0.16 × 0.15 mm
V = 1154.7 (4) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4484 independent reflections
Radiation source: fine-focus sealed tube3788 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 293(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −12→12
Tmin = 0.809, Tmax = 0.851k = −13→13
6797 measured reflectionsl = −10→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.123  w = 1/[σ2(Fo2) + (0.0391P)2 + 1.1151P] where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.001
4484 reflectionsΔρmax = 0.79 e Å3
318 parametersΔρmin = −0.42 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Zn10.69886 (4)0.81936 (4)0.62615 (4)0.02963 (15)
N10.8962 (3)0.7397 (3)0.6331 (3)0.0290 (7)
N20.7562 (3)0.9615 (3)0.6702 (3)0.0294 (7)
O10.7872 (3)1.0671 (3)0.1966 (3)0.0402 (7)
O20.7264 (3)0.9119 (3)0.4398 (3)0.0476 (7)
O30.7021 (4)0.7032 (3)0.4797 (3)0.0653 (10)
O40.5135 (3)1.1471 (4)0.2926 (4)0.0723 (11)
O50.4336 (4)1.3253 (4)0.1854 (5)0.0931 (15)
O1W0.6185 (5)0.4727 (3)0.6971 (4)0.0904 (14)
H1WA0.64060.52860.62190.109*
H1WB0.60350.51440.74940.109*
C10.5330 (5)1.2495 (5)0.1998 (6)0.0507 (12)
C20.6804 (4)1.2853 (4)0.1109 (4)0.0366 (9)
C30.7046 (5)1.4153 (4)0.0292 (5)0.0474 (11)
H30.62851.47580.02350.057*
C40.8373 (5)1.4565 (4)−0.0429 (5)0.0522 (12)
H40.85061.5438−0.09650.063*
C50.9501 (5)1.3685 (5)−0.0355 (4)0.0497 (12)
H51.04021.3968−0.08250.060*
C60.9309 (4)1.2378 (4)0.0413 (4)0.0400 (10)
H61.00781.17760.04410.048*
C70.7965 (4)1.1970 (4)0.1141 (4)0.0305 (8)
C80.7349 (4)0.9736 (3)0.1771 (4)0.0311 (8)
C90.7182 (4)0.9954 (4)0.0613 (4)0.0395 (10)
H90.73701.0770−0.00290.047*
C100.6740 (5)0.8971 (4)0.0415 (4)0.0469 (11)
H100.66110.9133−0.03540.056*
C110.6487 (5)0.7745 (4)0.1344 (5)0.0485 (11)
H110.62120.70710.12000.058*
C120.6650 (4)0.7535 (4)0.2488 (5)0.0432 (10)
H120.64760.67070.31130.052*
C130.7062 (4)0.8508 (4)0.2750 (4)0.0325 (8)
C140.7124 (4)0.8198 (4)0.4060 (4)0.0401 (10)
C150.9622 (4)0.6263 (3)0.6140 (4)0.0360 (9)
H150.91290.56880.60710.043*
C161.0999 (4)0.5905 (4)0.6042 (4)0.0375 (9)
H161.14120.51000.59170.045*
C171.1763 (4)0.6746 (4)0.6130 (4)0.0347 (9)
C181.3281 (5)0.6431 (5)0.5984 (6)0.0558 (13)
H18A1.33590.57990.67680.084*
H18B1.36990.72280.57960.084*
H18C1.37560.60650.52950.084*
C191.1067 (4)0.7924 (3)0.6351 (4)0.0311 (8)
H191.15400.85130.64250.037*
C200.9681 (4)0.8214 (3)0.6458 (3)0.0260 (8)
C210.8882 (4)0.9448 (3)0.6701 (3)0.0258 (7)
C220.9417 (4)1.0362 (3)0.6920 (3)0.0285 (8)
H221.03261.02220.69230.034*
C230.8611 (4)1.1487 (3)0.7136 (4)0.0329 (9)
C240.9184 (5)1.2489 (4)0.7370 (5)0.0450 (11)
H24A0.96781.20410.79530.068*
H24B0.84281.30550.77370.068*
H24C0.98121.30130.65720.068*
C250.7257 (4)1.1644 (4)0.7143 (4)0.0368 (9)
H250.66801.23840.72880.044*
C260.6775 (4)1.0689 (4)0.6931 (4)0.0371 (9)
H260.58601.07980.69490.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0253 (2)0.0322 (2)0.0321 (3)−0.00478 (16)−0.00982 (19)−0.01000 (19)
N10.0305 (17)0.0258 (15)0.0303 (17)−0.0043 (12)−0.0116 (15)−0.0061 (13)
N20.0243 (16)0.0322 (15)0.0351 (18)−0.0003 (12)−0.0112 (14)−0.0144 (14)
O10.0490 (18)0.0403 (15)0.0358 (16)−0.0131 (13)−0.0210 (14)−0.0053 (13)
O20.0485 (19)0.0604 (19)0.0336 (16)−0.0092 (15)−0.0156 (15)−0.0106 (15)
O30.076 (2)0.0526 (19)0.053 (2)−0.0105 (17)−0.033 (2)0.0133 (17)
O40.040 (2)0.113 (3)0.051 (2)−0.034 (2)−0.0021 (17)−0.013 (2)
O50.040 (2)0.069 (2)0.155 (5)0.0009 (18)−0.023 (3)−0.034 (3)
O1W0.115 (4)0.0360 (18)0.091 (3)0.000 (2)−0.016 (3)−0.014 (2)
C10.033 (3)0.051 (3)0.078 (4)−0.005 (2)−0.013 (3)−0.038 (3)
C20.031 (2)0.042 (2)0.039 (2)−0.0068 (17)−0.0070 (19)−0.0184 (19)
C30.051 (3)0.038 (2)0.053 (3)−0.0012 (19)−0.019 (2)−0.015 (2)
C40.073 (4)0.037 (2)0.042 (3)−0.021 (2)−0.014 (3)−0.006 (2)
C50.048 (3)0.061 (3)0.038 (2)−0.032 (2)−0.001 (2)−0.015 (2)
C60.030 (2)0.051 (2)0.039 (2)−0.0054 (18)−0.0098 (19)−0.016 (2)
C70.034 (2)0.0351 (19)0.0239 (19)−0.0122 (16)−0.0099 (17)−0.0072 (16)
C80.0245 (19)0.0331 (19)0.035 (2)−0.0020 (15)−0.0083 (17)−0.0120 (17)
C90.047 (3)0.042 (2)0.027 (2)−0.0101 (19)−0.012 (2)−0.0077 (18)
C100.052 (3)0.057 (3)0.041 (3)−0.004 (2)−0.017 (2)−0.025 (2)
C110.051 (3)0.042 (2)0.060 (3)−0.003 (2)−0.019 (2)−0.026 (2)
C120.035 (2)0.034 (2)0.053 (3)0.0008 (17)−0.011 (2)−0.012 (2)
C130.027 (2)0.0325 (19)0.034 (2)0.0011 (15)−0.0090 (18)−0.0096 (17)
C140.024 (2)0.050 (2)0.034 (2)−0.0015 (17)−0.0089 (18)−0.002 (2)
C150.043 (2)0.0257 (18)0.040 (2)−0.0070 (16)−0.015 (2)−0.0086 (17)
C160.043 (2)0.0263 (18)0.042 (2)0.0070 (16)−0.016 (2)−0.0138 (18)
C170.033 (2)0.036 (2)0.035 (2)0.0031 (16)−0.0127 (18)−0.0122 (18)
C180.039 (3)0.055 (3)0.085 (4)0.018 (2)−0.031 (3)−0.036 (3)
C190.032 (2)0.0329 (19)0.032 (2)0.0001 (15)−0.0148 (18)−0.0115 (17)
C200.0282 (19)0.0241 (16)0.0236 (18)−0.0021 (14)−0.0077 (16)−0.0068 (15)
C210.0258 (19)0.0260 (17)0.0230 (18)−0.0020 (14)−0.0065 (16)−0.0071 (15)
C220.028 (2)0.0301 (18)0.0272 (19)−0.0025 (15)−0.0100 (17)−0.0080 (16)
C230.039 (2)0.0294 (18)0.029 (2)−0.0051 (16)−0.0103 (18)−0.0085 (17)
C240.052 (3)0.038 (2)0.053 (3)−0.0059 (19)−0.017 (2)−0.023 (2)
C250.035 (2)0.0309 (19)0.044 (2)0.0037 (16)−0.013 (2)−0.0149 (19)
C260.027 (2)0.034 (2)0.051 (3)0.0043 (16)−0.014 (2)−0.0168 (19)

Geometric parameters (Å, °)

Zn1—O22.006 (3)C8—C131.405 (5)
Zn1—O4i2.053 (4)C9—C101.370 (6)
Zn1—N22.059 (3)C9—H90.9300
Zn1—N12.086 (3)C10—C111.379 (6)
Zn1—O5i2.295 (5)C10—H100.9300
Zn1—O32.495 (4)C11—C121.375 (6)
N1—C151.335 (5)C11—H110.9300
N1—C201.353 (4)C12—C131.391 (5)
N2—C261.335 (5)C12—H120.9300
N2—C211.350 (4)C13—C141.501 (6)
O1—C81.372 (4)C15—C161.378 (5)
O1—C71.389 (4)C15—H150.9300
O2—C141.261 (5)C16—C171.383 (5)
O3—C141.246 (5)C16—H160.9300
O4—C11.231 (6)C17—C191.399 (5)
O4—Zn1i2.053 (4)C17—C181.503 (5)
O5—C11.214 (5)C18—H18A0.9600
O5—Zn1i2.295 (5)C18—H18B0.9600
O1W—H1WA0.8500C18—H18C0.9600
O1W—H1WB0.8500C19—C201.380 (5)
C1—C21.512 (6)C19—H190.9300
C1—Zn1i2.519 (5)C20—C211.489 (5)
C2—C71.389 (5)C21—C221.378 (5)
C2—C31.395 (6)C22—C231.383 (5)
C3—C41.372 (6)C22—H220.9300
C3—H30.9300C23—C251.385 (5)
C4—C51.367 (7)C23—C241.497 (5)
C4—H40.9300C24—H24A0.9600
C5—C61.382 (6)C24—H24B0.9600
C5—H50.9300C24—H24C0.9600
C6—C71.386 (5)C25—C261.377 (5)
C6—H60.9300C25—H250.9300
C8—C91.392 (5)C26—H260.9300
O2—Zn1—O4i100.39 (14)C10—C9—C8120.3 (4)
O2—Zn1—N2100.84 (13)C10—C9—H9119.8
O4i—Zn1—N296.86 (14)C8—C9—H9119.8
O2—Zn1—N1106.07 (12)C9—C10—C11120.7 (4)
O4i—Zn1—N1153.52 (14)C9—C10—H10119.7
N2—Zn1—N179.25 (11)C11—C10—H10119.7
O2—Zn1—O5i145.16 (14)C12—C11—C10118.8 (4)
O4i—Zn1—O5i57.76 (14)C12—C11—H11120.6
N2—Zn1—O5i108.05 (15)C10—C11—H11120.6
N1—Zn1—O5i98.21 (12)C11—C12—C13122.8 (4)
O2—Zn1—O356.84 (11)C11—C12—H12118.6
O4i—Zn1—O399.09 (14)C13—C12—H12118.6
N2—Zn1—O3154.58 (12)C12—C13—C8117.0 (4)
N1—Zn1—O394.60 (12)C12—C13—C14118.4 (4)
O5i—Zn1—O397.20 (14)C8—C13—C14124.6 (4)
O2—Zn1—C1i124.65 (15)O3—C14—O2121.3 (4)
O4i—Zn1—C1i29.03 (14)O3—C14—C13119.1 (4)
N2—Zn1—C1i104.76 (13)O2—C14—C13119.6 (3)
N1—Zn1—C1i126.34 (15)N1—C15—C16123.2 (3)
O5i—Zn1—C1i28.74 (14)N1—C15—H15118.4
O3—Zn1—C1i98.76 (13)C16—C15—H15118.4
C15—N1—C20117.9 (3)C15—C16—C17119.7 (3)
C15—N1—Zn1127.7 (2)C15—C16—H16120.1
C20—N1—Zn1114.0 (2)C17—C16—H16120.1
C26—N2—C21118.4 (3)C16—C17—C19117.2 (3)
C26—N2—Zn1126.0 (2)C16—C17—C18122.2 (4)
C21—N2—Zn1115.5 (2)C19—C17—C18120.7 (4)
C8—O1—C7121.0 (3)C17—C18—H18A109.5
C14—O2—Zn1101.8 (3)C17—C18—H18B109.5
C14—O3—Zn179.6 (3)H18A—C18—H18B109.5
C1—O4—Zn1i97.0 (3)C17—C18—H18C109.5
C1—O5—Zn1i85.9 (4)H18A—C18—H18C109.5
H1WA—O1W—H1WB107.7H18B—C18—H18C109.5
O5—C1—O4119.3 (5)C20—C19—C17120.1 (3)
O5—C1—C2120.5 (5)C20—C19—H19119.9
O4—C1—C2120.1 (4)C17—C19—H19119.9
O5—C1—Zn1i65.3 (3)N1—C20—C19121.8 (3)
O4—C1—Zn1i54.0 (3)N1—C20—C21115.6 (3)
C2—C1—Zn1i171.7 (4)C19—C20—C21122.7 (3)
C7—C2—C3117.3 (4)N2—C21—C22121.3 (3)
C7—C2—C1122.8 (4)N2—C21—C20115.0 (3)
C3—C2—C1119.6 (4)C22—C21—C20123.7 (3)
C4—C3—C2122.0 (4)C21—C22—C23120.4 (3)
C4—C3—H3119.0C21—C22—H22119.8
C2—C3—H3119.0C23—C22—H22119.8
C5—C4—C3119.6 (4)C22—C23—C25117.8 (3)
C5—C4—H4120.2C22—C23—C24120.9 (3)
C3—C4—H4120.2C25—C23—C24121.4 (4)
C4—C5—C6120.4 (4)C23—C24—H24A109.5
C4—C5—H5119.8C23—C24—H24B109.5
C6—C5—H5119.8H24A—C24—H24B109.5
C5—C6—C7119.6 (4)C23—C24—H24C109.5
C5—C6—H6120.2H24A—C24—H24C109.5
C7—C6—H6120.2H24B—C24—H24C109.5
C6—C7—O1115.8 (3)C26—C25—C23119.2 (4)
C6—C7—C2121.0 (4)C26—C25—H25120.4
O1—C7—C2123.0 (3)C23—C25—H25120.4
O1—C8—C9121.5 (3)N2—C26—C25122.9 (3)
O1—C8—C13118.0 (3)N2—C26—H26118.5
C9—C8—C13120.3 (3)C25—C26—H26118.5
O2—Zn1—N1—C15−82.0 (3)C1—C2—C7—C6−172.7 (4)
O4i—Zn1—N1—C1595.9 (4)C3—C2—C7—O1176.2 (3)
N2—Zn1—N1—C15179.7 (3)C1—C2—C7—O11.9 (6)
O5i—Zn1—N1—C1572.7 (3)C7—O1—C8—C914.3 (6)
O3—Zn1—N1—C15−25.3 (3)C7—O1—C8—C13−169.4 (3)
C1i—Zn1—N1—C1579.1 (4)O1—C8—C9—C10175.9 (4)
O2—Zn1—N1—C2090.9 (3)C13—C8—C9—C10−0.3 (6)
O4i—Zn1—N1—C20−91.2 (4)C8—C9—C10—C11−1.5 (7)
N2—Zn1—N1—C20−7.4 (2)C9—C10—C11—C121.7 (7)
O5i—Zn1—N1—C20−114.4 (3)C10—C11—C12—C13−0.1 (7)
O3—Zn1—N1—C20147.7 (3)C11—C12—C13—C8−1.6 (6)
C1i—Zn1—N1—C20−107.9 (3)C11—C12—C13—C14176.4 (4)
O2—Zn1—N2—C2678.6 (3)O1—C8—C13—C12−174.5 (3)
O4i—Zn1—N2—C26−23.5 (4)C9—C8—C13—C121.8 (6)
N1—Zn1—N2—C26−176.9 (3)O1—C8—C13—C147.6 (6)
O5i—Zn1—N2—C26−81.7 (3)C9—C8—C13—C14−176.1 (4)
O3—Zn1—N2—C26105.1 (4)Zn1—O3—C14—O26.0 (4)
C1i—Zn1—N2—C26−51.9 (4)Zn1—O3—C14—C13−173.3 (3)
O2—Zn1—N2—C21−98.6 (3)Zn1—O2—C14—O3−7.5 (5)
O4i—Zn1—N2—C21159.4 (3)Zn1—O2—C14—C13171.8 (3)
N1—Zn1—N2—C215.9 (3)C12—C13—C14—O311.0 (6)
O5i—Zn1—N2—C21101.1 (3)C8—C13—C14—O3−171.1 (4)
O3—Zn1—N2—C21−72.0 (4)C12—C13—C14—O2−168.3 (4)
C1i—Zn1—N2—C21130.9 (3)C8—C13—C14—O29.6 (6)
O4i—Zn1—O2—C14−90.3 (3)C20—N1—C15—C16−1.4 (6)
N2—Zn1—O2—C14170.5 (2)Zn1—N1—C15—C16171.3 (3)
N1—Zn1—O2—C1488.7 (3)N1—C15—C16—C17−0.6 (6)
O5i—Zn1—O2—C14−43.6 (4)C15—C16—C17—C191.6 (6)
O3—Zn1—O2—C143.8 (2)C15—C16—C17—C18−177.8 (4)
C1i—Zn1—O2—C14−72.9 (3)C16—C17—C19—C20−0.7 (6)
O2—Zn1—O3—C14−3.8 (2)C18—C17—C19—C20178.8 (4)
O4i—Zn1—O3—C1492.7 (3)C15—N1—C20—C192.4 (5)
N2—Zn1—O3—C14−35.5 (4)Zn1—N1—C20—C19−171.3 (3)
N1—Zn1—O3—C14−110.0 (2)C15—N1—C20—C21−178.6 (3)
O5i—Zn1—O3—C14151.1 (2)Zn1—N1—C20—C217.8 (4)
C1i—Zn1—O3—C14122.1 (3)C17—C19—C20—N1−1.4 (6)
Zn1i—O5—C1—O41.9 (5)C17—C19—C20—C21179.6 (3)
Zn1i—O5—C1—C2−173.3 (4)C26—N2—C21—C22−0.5 (5)
Zn1i—O4—C1—O5−2.1 (5)Zn1—N2—C21—C22176.9 (3)
Zn1i—O4—C1—C2173.1 (3)C26—N2—C21—C20179.0 (3)
O5—C1—C2—C7−172.9 (5)Zn1—N2—C21—C20−3.6 (4)
O4—C1—C2—C712.0 (7)N1—C20—C21—N2−2.9 (5)
O5—C1—C2—C312.9 (7)C19—C20—C21—N2176.2 (3)
O4—C1—C2—C3−162.2 (4)N1—C20—C21—C22176.6 (3)
C7—C2—C3—C4−1.7 (7)C19—C20—C21—C22−4.3 (6)
C1—C2—C3—C4172.8 (4)N2—C21—C22—C23−0.6 (6)
C2—C3—C4—C50.1 (7)C20—C21—C22—C23179.9 (3)
C3—C4—C5—C61.8 (7)C21—C22—C23—C251.0 (6)
C4—C5—C6—C7−1.9 (7)C21—C22—C23—C24−179.8 (4)
C5—C6—C7—O1−174.8 (4)C22—C23—C25—C26−0.3 (6)
C5—C6—C7—C20.2 (6)C24—C23—C25—C26−179.5 (4)
C8—O1—C7—C6−113.1 (4)C21—N2—C26—C251.2 (6)
C8—O1—C7—C272.0 (5)Zn1—N2—C26—C25−175.9 (3)
C3—C2—C7—C61.6 (6)C23—C25—C26—N2−0.8 (6)

Symmetry codes: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O30.852.042.845 (5)158
O1W—H1WB···O5i0.852.072.876 (6)158

Symmetry codes: (i) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2127).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, W., Yao, L. & Tao, R. (2008). Acta Cryst. E64, m169. [PMC free article] [PubMed]

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