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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m422.
Published online 2008 January 25. doi:  10.1107/S1600536808002249
PMCID: PMC2960213

Aqua(4-hydroxy­benzoato-κO)(4-hydroxy­benzoato-κ2 O,O′)(1,10-phenanthroline-κ2 N,N′)zinc(II) monohydrate

Abstract

The Zn atom in the title compound, [Zn(C7H5O3)2(C12H8N2)(H2O)]·H2O, exists in a distorted cis-ZnN2O4 octa­hedral coordination geometry. One of the 4-hydroxy­benzoate anions chelates in a bidentate manner whereas the other is monodentate. The complex mol­ecules are linked through the uncoordinated water mol­ecules into a hydrogen-bonded sheet structure.

Related literature

For related zinc bis­(4-hydroxy­benzoate) structures containing an N-heterocycle, see: Hökelek & Necefouglu (1996 [triangle]); Nadzhafov et al. (1981 [triangle]); Necefoğlu et al. (2002 [triangle]); Wang & Okabe (2005 [triangle]); Zheng et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m422-scheme1.jpg

Experimental

Crystal data

  • [Zn(C7H5O3)2(C12H8N2)(H2O)]·H2O
  • M r = 555.83
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m422-efi1.jpg
  • a = 11.1169 (5) Å
  • b = 19.738 (1) Å
  • c = 11.5503 (6) Å
  • β = 106.298 (1)°
  • V = 2432.5 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.06 mm−1
  • T = 295 (2) K
  • 0.30 × 0.24 × 0.18 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.674, T max = 0.832
  • 23098 measured reflections
  • 5541 independent reflections
  • 3924 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.131
  • S = 1.08
  • 5541 reflections
  • 336 parameters
  • H-atom parameters constrained
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.88 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002249/hb2688sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002249/hb2688Isup2.hkl

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

Acknowledgments

We thank the Heilongjiang Province Natural Science Foundation (No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this work.

supplementary crystallographic information

Comment

The title compound, (I), extends the range of adducts of zinc bis(4-hydroxybenzoate) with N-heterocycles: For the N,N-diethylnicotinamide adduct, see: Hökelek & Necefouglu (1996). For the pyridine adduct, see; Nadzhafov et al. (1981). For the nicotinamide adduct, see: Necefoğlu et al. (2002). For the bis(2-pyridyl)amine adduct, see: Wang & Okabe (2005). For the benzimidazole adduct, see: Zheng et al. (2006).

The Zn atom in (I) adopts a distorted cis-ZnN2O4 coordination geometry. One of the 4-hydroxybenzoate anions chelates in an anisobidentate manner whereas the other is unidentate (Table 1, Fig. 1).

In the crystal, the complex molecules are linked through the uncoordinated water molecules into a hydrogen-bonded sheet structure (Table 2).

Experimental

Zinc diacetate dihydrate (1 mmol), 1,10-phenanthroline (2 mmol) and 4-hydroxybenzoic acid (2 mmol) were dissolved in aqueous ethanol Colourless blocks of (I) were isolated after several days.

Refinement

The carbon-bound and hydroxyl H atoms were placed in calculated positions (C–H = 0.93, O–H = 0.85 Å) and refined as riding with Uiso(H) 1.2–1.5Ueq(C, O). The water H atoms were placed in chemically reasonable positions with O—H = 0.85Å on the basis of likely hydrogen bonding interactions and refined as riding with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (H atoms drawn as spheres of arbitrary radius).

Crystal data

[Zn(C7H5O3)2(C12H8N2)(H2O)]·H2OF(000) = 1144
Mr = 555.83Dx = 1.518 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10359 reflections
a = 11.1169 (5) Åθ = 3.1–27.5°
b = 19.738 (1) ŵ = 1.06 mm1
c = 11.5503 (6) ÅT = 295 K
β = 106.298 (1)°Block, colorless
V = 2432.5 (2) Å30.30 × 0.24 × 0.18 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer5541 independent reflections
Radiation source: fine-focus sealed tube3924 reflections with I > 2σ(I)
graphiteRint = 0.036
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −25→25
Tmin = 0.674, Tmax = 0.832l = −14→14
23098 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0632P)2 + 0.8555P] where P = (Fo2 + 2Fc2)/3
5541 reflections(Δ/σ)max = 0.001
336 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = −0.88 e Å3

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

xyzUiso*/Ueq
Zn10.23086 (3)0.517846 (16)0.72570 (3)0.05090 (13)
O10.2083 (2)0.43474 (11)0.6190 (2)0.0681 (6)
O20.2863 (2)0.40272 (11)0.8070 (2)0.0663 (6)
O30.3803 (2)0.13818 (12)0.5298 (2)0.0729 (6)
H3o0.35480.13570.45330.109*
O40.19613 (18)0.60020 (9)0.61024 (17)0.0507 (4)
O50.3820 (2)0.61864 (13)0.5776 (2)0.0725 (6)
O60.03862 (19)0.81782 (11)0.19250 (19)0.0612 (5)
H6o0.09240.83920.16690.092*
O1w0.4267 (2)0.52299 (12)0.7387 (2)0.0749 (7)
H1w10.44830.48740.70800.112*
H1w20.44090.55760.70070.112*
O2w0.5117 (3)0.5725 (2)0.4171 (4)0.1517 (16)
H2w10.46230.57040.46140.182*
H2w20.49140.60470.36640.182*
N10.2575 (2)0.55676 (12)0.8980 (2)0.0524 (6)
N20.0408 (2)0.52319 (11)0.7369 (2)0.0478 (5)
C10.2581 (3)0.38959 (15)0.6961 (3)0.0555 (7)
C20.2870 (3)0.32281 (14)0.6520 (3)0.0498 (6)
C30.2367 (3)0.30452 (15)0.5320 (3)0.0559 (7)
H30.18300.33420.47950.067*
C40.2653 (3)0.24292 (16)0.4895 (3)0.0589 (7)
H40.22910.23080.40950.071*
C50.3479 (3)0.19928 (15)0.5664 (3)0.0549 (7)
C60.4005 (3)0.21700 (15)0.6863 (3)0.0574 (7)
H60.45630.18790.73810.069*
C70.3693 (3)0.27787 (15)0.7279 (3)0.0555 (7)
H70.40390.28930.80850.067*
C80.2667 (3)0.62967 (14)0.5549 (3)0.0495 (6)
C90.2074 (3)0.67968 (14)0.4592 (2)0.0480 (6)
C100.0776 (3)0.68671 (15)0.4180 (3)0.0539 (7)
H100.02690.65980.45080.065*
C110.0234 (3)0.73289 (16)0.3295 (3)0.0562 (7)
H11−0.06340.73700.30310.067*
C120.0982 (3)0.77342 (14)0.2796 (2)0.0509 (6)
C130.2280 (3)0.76739 (15)0.3202 (3)0.0562 (7)
H130.27860.79450.28740.067*
C140.2815 (3)0.72096 (14)0.4094 (3)0.0543 (7)
H140.36830.71720.43660.065*
C150.1503 (3)0.56991 (13)0.9281 (2)0.0501 (6)
C160.3666 (3)0.57100 (18)0.9768 (3)0.0701 (9)
H160.43990.56170.95600.084*
C170.3757 (4)0.5985 (2)1.0862 (4)0.0874 (12)
H170.45420.60701.13920.105*
C180.2708 (5)0.6137 (2)1.1192 (3)0.0868 (12)
H180.27740.63331.19400.104*
C190.1501 (4)0.59957 (16)1.0383 (3)0.0669 (9)
C200.0339 (5)0.61090 (19)1.0621 (4)0.0853 (12)
H200.03310.63061.13500.102*
C21−0.0760 (4)0.5941 (2)0.9824 (4)0.0843 (12)
H21−0.15050.60151.00220.101*
C22−0.0799 (3)0.56479 (16)0.8669 (3)0.0640 (8)
C23−0.1891 (4)0.5470 (2)0.7791 (4)0.0847 (12)
H23−0.26680.55470.79230.102*
C24−0.1823 (4)0.5185 (2)0.6742 (4)0.0856 (12)
H24−0.25510.50690.61500.103*
C25−0.0643 (3)0.50667 (18)0.6557 (3)0.0654 (8)
H25−0.06040.48660.58400.078*
C260.0332 (3)0.55205 (13)0.8411 (2)0.0472 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0592 (2)0.0422 (2)0.0576 (2)0.00058 (14)0.02675 (17)0.00114 (14)
O10.0915 (16)0.0451 (11)0.0708 (14)0.0159 (11)0.0279 (12)0.0032 (10)
O20.0923 (16)0.0487 (12)0.0629 (13)0.0041 (11)0.0302 (12)−0.0055 (10)
O30.0831 (16)0.0597 (13)0.0764 (14)0.0212 (12)0.0235 (13)−0.0112 (12)
O40.0592 (11)0.0410 (10)0.0603 (11)0.0033 (8)0.0306 (9)0.0069 (8)
O50.0613 (13)0.0814 (16)0.0829 (15)0.0100 (12)0.0336 (12)0.0261 (13)
O60.0682 (13)0.0559 (12)0.0626 (12)−0.0031 (10)0.0232 (10)0.0126 (10)
O1w0.0624 (14)0.0749 (16)0.0959 (18)0.0095 (11)0.0359 (13)0.0233 (13)
O2w0.140 (3)0.187 (4)0.162 (3)−0.004 (3)0.099 (3)−0.052 (3)
N10.0549 (14)0.0441 (13)0.0575 (13)−0.0065 (10)0.0145 (12)−0.0008 (11)
N20.0518 (13)0.0453 (12)0.0484 (12)−0.0067 (10)0.0174 (11)0.0025 (10)
C10.0639 (17)0.0443 (15)0.0639 (18)−0.0001 (13)0.0271 (15)0.0002 (14)
C20.0550 (15)0.0416 (14)0.0586 (16)0.0015 (12)0.0257 (13)0.0001 (12)
C30.0608 (17)0.0522 (17)0.0568 (16)0.0093 (14)0.0200 (14)0.0030 (13)
C40.0648 (18)0.0591 (18)0.0544 (16)0.0071 (15)0.0193 (15)−0.0058 (14)
C50.0582 (16)0.0458 (15)0.0656 (18)0.0065 (13)0.0254 (14)−0.0047 (14)
C60.0605 (17)0.0492 (16)0.0620 (17)0.0121 (13)0.0162 (14)0.0017 (14)
C70.0614 (17)0.0499 (16)0.0568 (16)0.0013 (13)0.0193 (14)−0.0018 (13)
C80.0573 (16)0.0418 (14)0.0552 (15)−0.0020 (12)0.0254 (14)−0.0023 (12)
C90.0580 (16)0.0409 (14)0.0505 (14)−0.0050 (12)0.0244 (13)−0.0025 (12)
C100.0591 (17)0.0531 (16)0.0557 (16)−0.0110 (13)0.0263 (14)0.0028 (13)
C110.0554 (16)0.0565 (17)0.0588 (17)−0.0053 (13)0.0197 (14)0.0047 (14)
C120.0654 (17)0.0408 (14)0.0511 (15)−0.0042 (12)0.0241 (14)−0.0017 (12)
C130.0648 (18)0.0468 (15)0.0663 (18)−0.0070 (13)0.0336 (15)0.0051 (14)
C140.0562 (16)0.0483 (16)0.0630 (17)−0.0055 (13)0.0242 (14)0.0016 (13)
C150.0711 (18)0.0350 (13)0.0475 (14)−0.0020 (12)0.0220 (14)0.0025 (11)
C160.068 (2)0.065 (2)0.071 (2)−0.0107 (17)0.0100 (17)−0.0038 (17)
C170.089 (3)0.088 (3)0.077 (2)−0.018 (2)0.009 (2)−0.005 (2)
C180.136 (4)0.065 (2)0.0498 (18)−0.021 (2)0.011 (2)−0.0128 (16)
C190.105 (3)0.0459 (17)0.0577 (18)0.0020 (17)0.0366 (19)−0.0015 (14)
C200.138 (4)0.063 (2)0.071 (2)0.011 (2)0.055 (3)−0.0033 (18)
C210.105 (3)0.068 (2)0.108 (3)0.026 (2)0.076 (3)0.017 (2)
C220.0641 (19)0.0555 (18)0.082 (2)0.0096 (15)0.0358 (18)0.0179 (16)
C230.062 (2)0.085 (3)0.115 (3)0.0119 (19)0.039 (2)0.032 (3)
C240.056 (2)0.092 (3)0.099 (3)−0.0126 (19)0.005 (2)0.020 (2)
C250.069 (2)0.066 (2)0.0607 (18)−0.0145 (16)0.0163 (16)0.0010 (15)
C260.0586 (16)0.0359 (13)0.0534 (15)0.0016 (11)0.0259 (13)0.0065 (11)

Geometric parameters (Å, °)

Zn1—O12.025 (2)C7—H70.9300
Zn1—O22.470 (2)C8—C91.490 (4)
Zn1—O42.069 (2)C9—C141.392 (4)
Zn1—O1w2.143 (2)C9—C101.394 (4)
Zn1—N12.075 (2)C10—C111.376 (4)
Zn1—N22.155 (2)C10—H100.9300
O1—C11.272 (4)C11—C121.391 (4)
O2—C11.257 (4)C11—H110.9300
O3—C51.359 (3)C12—C131.392 (4)
O3—H3o0.8501C13—C141.383 (4)
O4—C81.282 (3)C13—H130.9300
O5—C81.253 (3)C14—H140.9300
O6—C121.358 (3)C15—C191.402 (4)
O6—H6o0.8501C15—C261.447 (4)
O1w—H1w10.8500C16—C171.353 (6)
O1w—H1w20.8501C16—H160.9300
O2w—H2w10.8499C17—C181.358 (6)
O2w—H2w20.8500C17—H170.9300
N1—C161.326 (4)C18—C191.431 (5)
N1—C151.357 (4)C18—H180.9300
N2—C251.318 (4)C19—C201.412 (6)
N2—C261.356 (3)C20—C211.349 (6)
C1—C21.481 (4)C20—H200.9300
C2—C31.388 (4)C21—C221.443 (5)
C2—C71.394 (4)C21—H210.9300
C3—C41.381 (4)C22—C231.391 (5)
C3—H30.9300C22—C261.394 (4)
C4—C51.384 (4)C23—C241.357 (6)
C4—H40.9300C23—H230.9300
C5—C61.389 (4)C24—C251.406 (6)
C6—C71.374 (4)C24—H240.9300
C6—H60.9300C25—H250.9300
O1—Zn1—O4105.98 (8)O4—C8—C9117.7 (2)
O1—Zn1—N1147.52 (9)C14—C9—C10118.4 (3)
O4—Zn1—N1106.14 (8)C14—C9—C8120.3 (3)
O1—Zn1—O1w91.75 (10)C10—C9—C8121.3 (2)
O4—Zn1—O1w90.57 (8)C11—C10—C9121.1 (3)
N1—Zn1—O1w92.66 (10)C11—C10—H10119.5
O1—Zn1—N296.91 (9)C9—C10—H10119.5
O4—Zn1—N289.51 (8)C10—C11—C12120.0 (3)
N1—Zn1—N278.65 (9)C10—C11—H11120.0
O1w—Zn1—N2170.97 (10)C12—C11—H11120.0
O1—Zn1—O257.39 (8)O6—C12—C11117.0 (3)
O4—Zn1—O2161.68 (7)O6—C12—C13123.3 (3)
N1—Zn1—O291.30 (8)C11—C12—C13119.7 (3)
O1w—Zn1—O282.91 (8)C14—C13—C12119.7 (3)
N2—Zn1—O299.59 (8)C14—C13—H13120.1
C1—O1—Zn1100.74 (19)C12—C13—H13120.1
C1—O2—Zn180.68 (17)C13—C14—C9121.1 (3)
C5—O3—H3o109.5C13—C14—H14119.5
C8—O4—Zn1130.40 (18)C9—C14—H14119.5
C12—O6—H6o109.5N1—C15—C19122.5 (3)
Zn1—O1w—H1w1109.4N1—C15—C26117.3 (2)
Zn1—O1w—H1w2109.5C19—C15—C26120.1 (3)
H1w1—O1w—H1w2109.5N1—C16—C17122.7 (4)
H2w1—O2w—H2w2111.0N1—C16—H16118.7
C16—N1—C15118.9 (3)C17—C16—H16118.7
C16—N1—Zn1126.4 (2)C16—C17—C18120.4 (4)
C15—N1—Zn1114.65 (18)C16—C17—H17119.8
C25—N2—C26118.2 (3)C18—C17—H17119.8
C25—N2—Zn1129.3 (2)C17—C18—C19119.6 (3)
C26—N2—Zn1112.33 (18)C17—C18—H18120.2
O2—C1—O1120.3 (3)C19—C18—H18120.2
O2—C1—C2121.2 (3)C15—C19—C20118.5 (3)
O1—C1—C2118.5 (3)C15—C19—C18115.8 (3)
O2—C1—Zn170.63 (16)C20—C19—C18125.7 (3)
O1—C1—Zn150.35 (14)C21—C20—C19122.1 (3)
C2—C1—Zn1164.2 (2)C21—C20—H20118.9
C3—C2—C7118.2 (3)C19—C20—H20118.9
C3—C2—C1120.6 (3)C20—C21—C22121.0 (3)
C7—C2—C1121.2 (3)C20—C21—H21119.5
C4—C3—C2121.0 (3)C22—C21—H21119.5
C4—C3—H3119.5C23—C22—C26117.0 (3)
C2—C3—H3119.5C23—C22—C21124.7 (3)
C3—C4—C5119.8 (3)C26—C22—C21118.3 (3)
C3—C4—H4120.1C24—C23—C22120.0 (3)
C5—C4—H4120.1C24—C23—H23120.0
O3—C5—C4122.6 (3)C22—C23—H23120.0
O3—C5—C6117.3 (3)C23—C24—C25119.5 (4)
C4—C5—C6120.0 (3)C23—C24—H24120.2
C7—C6—C5119.5 (3)C25—C24—H24120.2
C7—C6—H6120.3N2—C25—C24122.0 (4)
C5—C6—H6120.3N2—C25—H25119.0
C6—C7—C2121.5 (3)C24—C25—H25119.0
C6—C7—H7119.3N2—C26—C22123.4 (3)
C2—C7—H7119.3N2—C26—C15116.8 (2)
O5—C8—O4123.4 (3)C22—C26—C15119.8 (3)
O5—C8—C9118.9 (2)
O4—Zn1—O1—C1166.06 (18)C1—C2—C7—C6−177.4 (3)
N1—Zn1—O1—C1−22.8 (3)Zn1—O4—C8—O5−11.7 (4)
O1w—Zn1—O1—C175.0 (2)Zn1—O4—C8—C9168.48 (17)
N2—Zn1—O1—C1−102.5 (2)O5—C8—C9—C14−9.9 (4)
O2—Zn1—O1—C1−5.47 (18)O4—C8—C9—C14169.9 (3)
O1—Zn1—O2—C15.51 (18)O5—C8—C9—C10170.5 (3)
O4—Zn1—O2—C1−21.3 (3)O4—C8—C9—C10−9.7 (4)
N1—Zn1—O2—C1176.32 (19)C14—C9—C10—C110.5 (4)
O1w—Zn1—O2—C1−91.16 (19)C8—C9—C10—C11−179.9 (3)
N2—Zn1—O2—C197.61 (19)C9—C10—C11—C120.1 (5)
O1—Zn1—O4—C8−80.1 (2)C10—C11—C12—O6179.9 (3)
N1—Zn1—O4—C8104.8 (2)C10—C11—C12—C13−0.5 (4)
O1w—Zn1—O4—C811.9 (2)O6—C12—C13—C14179.9 (3)
N2—Zn1—O4—C8−177.1 (2)C11—C12—C13—C140.3 (4)
O2—Zn1—O4—C8−56.9 (4)C12—C13—C14—C90.3 (5)
C1—Zn1—O4—C8−70.8 (3)C10—C9—C14—C13−0.7 (4)
O1—Zn1—N1—C1692.9 (3)C8—C9—C14—C13179.7 (3)
O4—Zn1—N1—C16−95.9 (3)C16—N1—C15—C191.6 (4)
O1w—Zn1—N1—C16−4.6 (3)Zn1—N1—C15—C19−176.6 (2)
N2—Zn1—N1—C16177.9 (3)C16—N1—C15—C26−178.4 (3)
O2—Zn1—N1—C1678.4 (3)Zn1—N1—C15—C263.4 (3)
C1—Zn1—N1—C1680.4 (3)C15—N1—C16—C17−0.3 (5)
O1—Zn1—N1—C15−89.0 (3)Zn1—N1—C16—C17177.7 (3)
O4—Zn1—N1—C1582.14 (19)N1—C16—C17—C18−1.0 (6)
O1w—Zn1—N1—C15173.51 (19)C16—C17—C18—C191.0 (6)
N2—Zn1—N1—C15−4.01 (18)N1—C15—C19—C20−179.6 (3)
O2—Zn1—N1—C15−103.54 (19)C26—C15—C19—C200.5 (4)
C1—Zn1—N1—C15−101.5 (2)N1—C15—C19—C18−1.5 (4)
O1—Zn1—N2—C25−33.1 (3)C26—C15—C19—C18178.5 (3)
O4—Zn1—N2—C2573.0 (3)C17—C18—C19—C150.2 (5)
N1—Zn1—N2—C25179.5 (3)C17—C18—C19—C20178.1 (4)
O2—Zn1—N2—C25−91.1 (3)C15—C19—C20—C210.1 (5)
C1—Zn1—N2—C25−62.0 (3)C18—C19—C20—C21−177.8 (4)
O1—Zn1—N2—C26151.55 (17)C19—C20—C21—C22−1.4 (6)
O4—Zn1—N2—C26−102.41 (18)C20—C21—C22—C23−178.9 (4)
N1—Zn1—N2—C264.16 (17)C20—C21—C22—C262.2 (5)
O2—Zn1—N2—C2693.56 (17)C26—C22—C23—C240.2 (5)
C1—Zn1—N2—C26122.68 (18)C21—C22—C23—C24−178.7 (4)
Zn1—O2—C1—O1−8.6 (3)C22—C23—C24—C250.5 (6)
Zn1—O2—C1—C2168.4 (3)C26—N2—C25—C240.4 (5)
Zn1—O1—C1—O210.5 (3)Zn1—N2—C25—C24−174.8 (2)
Zn1—O1—C1—C2−166.6 (2)C23—C24—C25—N2−0.8 (6)
O2—C1—C2—C3168.8 (3)C25—N2—C26—C220.3 (4)
O1—C1—C2—C3−14.2 (4)Zn1—N2—C26—C22176.3 (2)
O2—C1—C2—C7−14.0 (4)C25—N2—C26—C15−179.7 (3)
O1—C1—C2—C7163.1 (3)Zn1—N2—C26—C15−3.7 (3)
C7—C2—C3—C41.3 (4)C23—C22—C26—N2−0.6 (4)
C1—C2—C3—C4178.7 (3)C21—C22—C26—N2178.3 (3)
C2—C3—C4—C5−1.8 (5)C23—C22—C26—C15179.4 (3)
C3—C4—C5—O3−179.6 (3)C21—C22—C26—C15−1.7 (4)
C3—C4—C5—C61.0 (5)N1—C15—C26—N20.4 (4)
O3—C5—C6—C7−179.1 (3)C19—C15—C26—N2−179.6 (2)
C4—C5—C6—C70.3 (5)N1—C15—C26—C22−179.6 (2)
C5—C6—C7—C2−0.8 (5)C19—C15—C26—C220.4 (4)
C3—C2—C7—C60.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3o···O2i0.851.812.619 (3)157
O6—H6o···O4ii0.851.902.742 (3)171
O1w—H1w1···O2wiii0.852.012.819 (4)158
O1w—H1w2···O50.851.842.599 (3)148
O2w—H2w1···O50.852.042.801 (4)148

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2688).

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