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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1426.
Published online 2009 October 23. doi:  10.1107/S160053680904313X
PMCID: PMC2971229

Bis(5,5-diphenyl­hydantoinato-κN 3)(ethyl­enediamine)zinc(II)

Abstract

In the title compound, [Zn(C15H11N2O2)2(C2H8N2)], the ZnII atom is coordinated in a distorted tetra­hedral geometry. Intra­molecular N—H(...)O, C—H(...)O and C—H(...)N hydrogen bonds occur. In the crystal, mol­ecules are linked by inter­molecular N—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

5,5-Diphenyl­imidazoline-2,4-dione (phenytoin) is widely used in the treatment of epilepsy and should be an excellent ligand for transition metal complexes, see: Milne et al. (1999 [triangle]); Akitsu & Einaga (2005 [triangle]); Akitsu et al. (1997 [triangle]). For complexes with 5,5-diphenyl­hydantoinate, see: Hu, Xu, Wang & Xu (2006 [triangle]); Hu, Xu, Xu & Wang (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1426-scheme1.jpg

Experimental

Crystal data

  • [Zn(C15H11N2O2)2(C2H8N2)]
  • M r = 627.99
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1426-efi1.jpg
  • a = 9.702 (1) Å
  • b = 13.052 (2) Å
  • c = 13.293 (2) Å
  • α = 109.114 (2)°
  • β = 109.462 (2)°
  • γ = 93.020(10)°
  • V = 1473.1 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.88 mm−1
  • T = 298 K
  • 0.50 × 0.46 × 0.32 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.667, T max = 0.766
  • 7725 measured reflections
  • 5124 independent reflections
  • 4452 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.089
  • S = 1.03
  • 5124 reflections
  • 388 parameters
  • H-atom parameters constrained
  • Δρmax = 0.61 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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/S160053680904313X/bx2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904313X/bx2240Isup2.hkl

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

Acknowledgments

We are grateful for the financial support from the Key Project for Fundamental Research of the Education Committee of Jiangsu Province (07KJA15011) and the Natural Science Foundation of Huaihai Institute of Technology (KX07042).

supplementary crystallographic information

Comment

5,5-diphenylimidazoline-2,4-dione (phenytoin) compound is a widely used drug in the treatment of epilepsy and should be an excellent ligand for transition metal complex (Milne et al., 1999; Akitsu, Komorita, Kushi et al.,1997; Akitsu, Einaga, 2005). We have designed and synthesized a series of complexes with 5,5-diphenylhydantoinate (Hu, Xu, Wang et al., 2006). We report here the crystal structure of the title compound (I). The compound (Fig. 1) consists of [Zn(pht)2(en)] (pht=5,5-diphenylhydantoinato; en=ethylendiamine) complex neutral molecule. The Zn atom is coordinated by two nitrogen atoms from two pht ligands and two nitrogen atoms from two en ligands and is in a distorted tetrahedron ZnN4 coordination environment.The Zn—N bond distances lie in the range of 1.9506 (18)Å to 2.057 (2) Å. There are intra- and intermolecular N—H···O=C hydrogen bonds, forming a three-dimensional network in the crystal structure, Table 1.

Experimental

To a solution of pht (1.00 mmol) in methanol (10 ml) was added zinc(II) acetate tetrahydrate (0.5 mmol) and the solution of Ethylenediamine(0.5 mmol) in methanol (10 ml). Then the mixture was sealed in a 25 ml stainless steel vessel with Teflon linear and heated to 393 K for 50 h the fill rate being 80%. After cooling to room temperature, the colorless single crystals were obtained by slow evaporation from the filtrate.

Refinement

The space group was uniquely assigned from the systematic absences. All H atoms were placed at calculated positions, with N—H = 0.86–0.90 Å, and with Uiso(H) values were set at 1.2Ueq, and C—H = 0.93Å (phenyl), 0.97Å (methylene), respectively, and with Uiso(H) values were set at 1.2 Ueq(C) (phenyl,methylene).

Figures

Fig. 1.
The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. The H-atom have been omitted for clarity.

Crystal data

[Zn(C15H11N2O2)2(C2H8N2)]Z = 2
Mr = 627.99F(000) = 652
Triclinic, P1Dx = 1.416 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.702 (1) ÅCell parameters from 4727 reflections
b = 13.0520 (15) Åθ = 2.6–27.7°
c = 13.2930 (16) ŵ = 0.88 mm1
α = 109.114 (2)°T = 298 K
β = 109.462 (2)°Block, colorless
γ = 93.302 (1)°0.50 × 0.46 × 0.32 mm
V = 1473.1 (3) Å3

Data collection

Bruker SMART CCD area-detector diffractometer5124 independent reflections
Radiation source: fine-focus sealed tube4452 reflections with I > 2σ(I)
graphiteRint = 0.017
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.667, Tmax = 0.766k = −15→15
7725 measured reflectionsl = −14→15

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0432P)2 + 0.9132P] where P = (Fo2 + 2Fc2)/3
5124 reflections(Δ/σ)max = 0.001
388 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = −0.45 e Å3

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
Zn1−0.00468 (3)0.61290 (2)0.37871 (2)0.02823 (10)
N10.4053 (2)0.53299 (18)0.37370 (16)0.0358 (5)
H10.48940.51540.40320.043*
N20.1898 (2)0.59269 (15)0.36211 (16)0.0290 (4)
N3−0.0141 (3)0.92085 (15)0.58602 (18)0.0380 (5)
H30.00400.99100.60280.046*
N4−0.0279 (2)0.74051 (15)0.49503 (17)0.0328 (4)
N5−0.1098 (2)0.46617 (15)0.36800 (17)0.0335 (4)
H5A−0.04320.42280.38350.040*
H5B−0.15480.47870.41900.040*
N6−0.1472 (2)0.5694 (2)0.21093 (19)0.0480 (6)
H6A−0.22880.59980.20670.058*
H6B−0.10200.59060.16990.058*
O10.33097 (18)0.56196 (14)0.52547 (13)0.0337 (4)
O20.1300 (2)0.61465 (16)0.18764 (15)0.0455 (5)
O30.0303 (2)0.86389 (14)0.41865 (17)0.0510 (5)
O4−0.1104 (2)0.66928 (13)0.60608 (16)0.0401 (4)
C10.3111 (2)0.56151 (18)0.42891 (19)0.0278 (5)
C20.2089 (3)0.5866 (2)0.2636 (2)0.0318 (5)
C30.3484 (3)0.5354 (2)0.25864 (19)0.0319 (5)
C40.2992 (3)0.4187 (2)0.1657 (2)0.0333 (5)
C50.3729 (3)0.3350 (2)0.1842 (2)0.0433 (6)
H50.45270.34990.25280.052*
C60.3292 (4)0.2292 (2)0.1016 (3)0.0537 (7)
H60.38070.17410.11510.064*
C70.2103 (4)0.2046 (2)−0.0001 (3)0.0523 (7)
H70.18120.1334−0.05500.063*
C80.1354 (3)0.2864 (2)−0.0196 (2)0.0498 (7)
H80.05450.2705−0.08780.060*
C90.1796 (3)0.3926 (2)0.0618 (2)0.0420 (6)
H90.12880.44760.04700.050*
C100.4530 (3)0.6143 (2)0.2406 (2)0.0325 (5)
C110.5446 (3)0.7065 (2)0.3331 (2)0.0440 (6)
H110.54780.71630.40640.053*
C120.6311 (3)0.7837 (2)0.3181 (3)0.0490 (7)
H120.69190.84470.38110.059*
C130.6278 (3)0.7708 (2)0.2107 (3)0.0500 (7)
H130.68520.82330.20060.060*
C140.5390 (3)0.6797 (3)0.1181 (3)0.0553 (8)
H140.53640.67060.04510.066*
C150.4527 (3)0.6011 (2)0.1331 (2)0.0469 (7)
H150.39430.53910.07010.056*
C16−0.0009 (3)0.84551 (19)0.4940 (2)0.0346 (6)
C17−0.0734 (3)0.74627 (18)0.5818 (2)0.0303 (5)
C18−0.0629 (3)0.86969 (18)0.6538 (2)0.0313 (5)
C19−0.2101 (3)0.89940 (19)0.6608 (2)0.0341 (5)
C20−0.2238 (4)1.0100 (2)0.6886 (3)0.0608 (9)
H20−0.14371.06300.70390.073*
C21−0.3546 (5)1.0409 (3)0.6938 (4)0.0841 (13)
H21−0.36231.11500.71340.101*
C22−0.4754 (4)0.9628 (3)0.6699 (4)0.0769 (11)
H22−0.56510.98390.67090.092*
C23−0.4618 (3)0.8539 (3)0.6447 (3)0.0568 (8)
H23−0.54220.80110.62950.068*
C24−0.3285 (3)0.8228 (2)0.6420 (2)0.0422 (6)
H24−0.31900.74940.62740.051*
C250.0588 (3)0.89167 (19)0.7714 (2)0.0357 (6)
C260.2070 (3)0.9131 (2)0.7872 (3)0.0530 (7)
H260.23290.92170.72860.064*
C270.3172 (4)0.9218 (3)0.8887 (3)0.0681 (10)
H270.41660.93670.89820.082*
C280.2816 (4)0.9088 (3)0.9754 (3)0.0697 (10)
H280.35620.91371.04330.084*
C290.1353 (4)0.8884 (3)0.9616 (3)0.0718 (10)
H290.11040.88031.02080.086*
C300.0239 (3)0.8797 (3)0.8599 (3)0.0554 (8)
H30−0.07530.86570.85120.066*
C31−0.2203 (4)0.4122 (3)0.2507 (3)0.0715 (10)
H31A−0.22610.33300.22750.086*
H31B−0.31720.42770.24990.086*
C32−0.1855 (5)0.4482 (3)0.1696 (3)0.0890 (14)
H32A−0.27030.42160.09750.107*
H32B−0.10240.41670.15570.107*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.03145 (16)0.02810 (15)0.03137 (16)0.01168 (11)0.01542 (12)0.01390 (11)
N10.0317 (11)0.0594 (13)0.0302 (11)0.0233 (10)0.0153 (9)0.0273 (10)
N20.0279 (10)0.0367 (10)0.0280 (10)0.0121 (8)0.0125 (8)0.0160 (8)
N30.0587 (14)0.0218 (9)0.0486 (13)0.0109 (9)0.0358 (11)0.0151 (9)
N40.0423 (12)0.0242 (9)0.0404 (11)0.0116 (9)0.0239 (10)0.0127 (9)
N50.0362 (11)0.0334 (10)0.0375 (11)0.0081 (9)0.0163 (9)0.0185 (9)
N60.0366 (13)0.0734 (16)0.0464 (13)0.0160 (12)0.0117 (11)0.0402 (13)
O10.0337 (9)0.0471 (10)0.0257 (8)0.0093 (7)0.0127 (7)0.0183 (7)
O20.0418 (11)0.0743 (13)0.0428 (10)0.0326 (10)0.0212 (9)0.0405 (10)
O30.0859 (15)0.0372 (10)0.0595 (12)0.0229 (10)0.0542 (12)0.0252 (9)
O40.0506 (11)0.0293 (9)0.0547 (11)0.0117 (8)0.0299 (9)0.0222 (8)
C10.0269 (12)0.0297 (11)0.0285 (12)0.0061 (9)0.0102 (10)0.0128 (10)
C20.0284 (12)0.0412 (13)0.0326 (13)0.0129 (10)0.0130 (10)0.0193 (11)
C30.0291 (13)0.0496 (14)0.0273 (12)0.0168 (11)0.0129 (10)0.0231 (11)
C40.0311 (13)0.0462 (14)0.0347 (13)0.0105 (11)0.0181 (11)0.0232 (11)
C50.0392 (15)0.0525 (16)0.0471 (15)0.0186 (13)0.0187 (13)0.0253 (13)
C60.061 (2)0.0490 (17)0.066 (2)0.0235 (15)0.0309 (17)0.0291 (15)
C70.064 (2)0.0444 (16)0.0512 (17)0.0022 (14)0.0278 (16)0.0163 (14)
C80.0516 (18)0.0568 (17)0.0396 (15)0.0017 (14)0.0126 (13)0.0219 (14)
C90.0432 (16)0.0499 (16)0.0390 (14)0.0127 (12)0.0145 (12)0.0240 (13)
C100.0271 (12)0.0461 (14)0.0335 (13)0.0159 (11)0.0146 (10)0.0213 (11)
C110.0457 (16)0.0524 (16)0.0381 (14)0.0149 (13)0.0185 (13)0.0181 (13)
C120.0421 (16)0.0460 (16)0.0527 (17)0.0083 (13)0.0136 (13)0.0146 (13)
C130.0414 (16)0.0540 (17)0.067 (2)0.0096 (13)0.0243 (15)0.0329 (16)
C140.0559 (19)0.073 (2)0.0485 (17)0.0045 (16)0.0241 (15)0.0330 (16)
C150.0444 (16)0.0629 (18)0.0347 (14)−0.0003 (13)0.0147 (12)0.0215 (13)
C160.0427 (15)0.0273 (12)0.0445 (14)0.0128 (10)0.0267 (12)0.0148 (11)
C170.0305 (13)0.0267 (11)0.0373 (13)0.0088 (10)0.0148 (10)0.0134 (10)
C180.0386 (14)0.0249 (11)0.0377 (13)0.0078 (10)0.0212 (11)0.0131 (10)
C190.0419 (14)0.0357 (13)0.0344 (13)0.0146 (11)0.0207 (11)0.0171 (11)
C200.068 (2)0.0454 (16)0.101 (3)0.0266 (15)0.057 (2)0.0371 (17)
C210.094 (3)0.067 (2)0.153 (4)0.055 (2)0.088 (3)0.067 (3)
C220.065 (2)0.093 (3)0.123 (3)0.050 (2)0.063 (2)0.069 (3)
C230.0432 (17)0.071 (2)0.068 (2)0.0131 (15)0.0288 (16)0.0306 (17)
C240.0461 (16)0.0405 (14)0.0478 (16)0.0121 (12)0.0248 (13)0.0179 (12)
C250.0374 (14)0.0278 (12)0.0418 (14)0.0053 (10)0.0180 (12)0.0096 (11)
C260.0434 (17)0.0584 (18)0.0517 (17)0.0047 (14)0.0224 (14)0.0095 (14)
C270.0370 (17)0.078 (2)0.069 (2)0.0039 (16)0.0139 (16)0.0100 (19)
C280.055 (2)0.070 (2)0.060 (2)0.0040 (17)−0.0032 (17)0.0200 (18)
C290.062 (2)0.100 (3)0.0502 (19)−0.002 (2)0.0093 (17)0.0381 (19)
C300.0393 (16)0.080 (2)0.0496 (17)0.0003 (15)0.0144 (14)0.0311 (16)
C310.078 (2)0.059 (2)0.053 (2)−0.0192 (18)0.0014 (18)0.0198 (16)
C320.110 (3)0.081 (3)0.0382 (18)−0.027 (2)−0.0048 (19)0.0157 (18)

Geometric parameters (Å, °)

Zn1—N41.9506 (18)C11—C121.381 (4)
Zn1—N21.9941 (19)C11—H110.9300
Zn1—N52.0561 (19)C12—C131.370 (4)
Zn1—N62.057 (2)C12—H120.9300
N1—C11.349 (3)C13—C141.374 (4)
N1—C31.455 (3)C13—H130.9300
N1—H10.8600C14—C151.392 (4)
N2—C21.360 (3)C14—H140.9300
N2—C11.390 (3)C15—H150.9300
N3—C161.346 (3)C17—C181.558 (3)
N3—C181.457 (3)C18—C191.525 (3)
N3—H30.8600C18—C251.535 (4)
N4—C171.348 (3)C19—C241.377 (4)
N4—C161.386 (3)C19—C201.394 (4)
N5—C311.469 (4)C20—C211.370 (4)
N5—H5A0.9000C20—H200.9300
N5—H5B0.9000C21—C221.384 (5)
N6—C321.472 (4)C21—H210.9300
N6—H6A0.9000C22—C231.374 (5)
N6—H6B0.9000C22—H220.9300
O1—C11.231 (3)C23—C241.386 (4)
O2—C21.224 (3)C23—H230.9300
O3—C161.226 (3)C24—H240.9300
O4—C171.221 (3)C25—C301.379 (4)
C2—C31.555 (3)C25—C261.380 (4)
C3—C101.534 (3)C26—C271.379 (5)
C3—C41.537 (3)C26—H260.9300
C4—C51.384 (3)C27—C281.365 (5)
C4—C91.396 (4)C27—H270.9300
C5—C61.386 (4)C28—C291.368 (5)
C5—H50.9300C28—H280.9300
C6—C71.377 (4)C29—C301.386 (4)
C6—H60.9300C29—H290.9300
C7—C81.371 (4)C30—H300.9300
C7—H70.9300C31—C321.433 (5)
C8—C91.384 (4)C31—H31A0.9700
C8—H80.9300C31—H31B0.9700
C9—H90.9300C32—H32A0.9700
C10—C151.382 (3)C32—H32B0.9700
C10—C111.389 (4)
N4—Zn1—N2123.12 (8)C12—C13—C14119.5 (3)
N4—Zn1—N5112.66 (8)C12—C13—H13120.2
N2—Zn1—N5108.94 (8)C14—C13—H13120.2
N4—Zn1—N6118.42 (9)C13—C14—C15120.3 (3)
N2—Zn1—N6102.08 (9)C13—C14—H14119.8
N5—Zn1—N684.83 (9)C15—C14—H14119.8
C1—N1—C3112.29 (18)C10—C15—C14120.7 (3)
C1—N1—H1123.9C10—C15—H15119.7
C3—N1—H1123.9C14—C15—H15119.7
C2—N2—C1108.39 (18)O3—C16—N3126.6 (2)
C2—N2—Zn1120.78 (15)O3—C16—N4123.3 (2)
C1—N2—Zn1129.63 (15)N3—C16—N4110.1 (2)
C16—N3—C18112.08 (19)O4—C17—N4126.9 (2)
C16—N3—H3124.0O4—C17—C18123.8 (2)
C18—N3—H3124.0N4—C17—C18109.18 (18)
C17—N4—C16109.22 (18)N3—C18—C19111.23 (19)
C17—N4—Zn1130.24 (15)N3—C18—C25112.6 (2)
C16—N4—Zn1120.51 (16)C19—C18—C25113.46 (19)
C31—N5—Zn1107.60 (17)N3—C18—C1799.11 (17)
C31—N5—H5A110.2C19—C18—C17114.35 (19)
Zn1—N5—H5A110.2C25—C18—C17105.10 (18)
C31—N5—H5B110.2C24—C19—C20118.8 (2)
Zn1—N5—H5B110.2C24—C19—C18123.3 (2)
H5A—N5—H5B108.5C20—C19—C18117.9 (2)
C32—N6—Zn1103.62 (18)C21—C20—C19120.3 (3)
C32—N6—H6A111.0C21—C20—H20119.8
Zn1—N6—H6A111.0C19—C20—H20119.8
C32—N6—H6B111.0C20—C21—C22120.6 (3)
Zn1—N6—H6B111.0C20—C21—H21119.7
H6A—N6—H6B109.0C22—C21—H21119.7
O1—C1—N1124.9 (2)C23—C22—C21119.5 (3)
O1—C1—N2124.9 (2)C23—C22—H22120.3
N1—C1—N2110.25 (19)C21—C22—H22120.3
O2—C2—N2127.1 (2)C22—C23—C24120.0 (3)
O2—C2—C3123.4 (2)C22—C23—H23120.0
N2—C2—C3109.58 (18)C24—C23—H23120.0
N1—C3—C10112.7 (2)C19—C24—C23120.7 (3)
N1—C3—C4111.98 (19)C19—C24—H24119.7
C10—C3—C4114.11 (18)C23—C24—H24119.7
N1—C3—C298.85 (17)C30—C25—C26118.3 (3)
C10—C3—C2108.59 (19)C30—C25—C18121.1 (2)
C4—C3—C2109.47 (19)C26—C25—C18120.3 (2)
C5—C4—C9117.7 (2)C27—C26—C25120.7 (3)
C5—C4—C3120.1 (2)C27—C26—H26119.6
C9—C4—C3122.2 (2)C25—C26—H26119.6
C4—C5—C6120.8 (3)C28—C27—C26120.5 (3)
C4—C5—H5119.6C28—C27—H27119.7
C6—C5—H5119.6C26—C27—H27119.7
C7—C6—C5120.8 (3)C27—C28—C29119.5 (3)
C7—C6—H6119.6C27—C28—H28120.2
C5—C6—H6119.6C29—C28—H28120.2
C8—C7—C6119.3 (3)C28—C29—C30120.3 (3)
C8—C7—H7120.4C28—C29—H29119.9
C6—C7—H7120.4C30—C29—H29119.9
C7—C8—C9120.3 (3)C25—C30—C29120.6 (3)
C7—C8—H8119.8C25—C30—H30119.7
C9—C8—H8119.8C29—C30—H30119.7
C8—C9—C4121.1 (3)C32—C31—N5112.7 (3)
C8—C9—H9119.4C32—C31—H31A109.1
C4—C9—H9119.4N5—C31—H31A109.1
C15—C10—C11118.0 (2)C32—C31—H31B109.1
C15—C10—C3122.0 (2)N5—C31—H31B109.1
C11—C10—C3119.8 (2)H31A—C31—H31B107.8
C12—C11—C10121.1 (3)C31—C32—N6111.7 (3)
C12—C11—H11119.4C31—C32—H32A109.3
C10—C11—H11119.4N6—C32—H32A109.3
C13—C12—C11120.3 (3)C31—C32—H32B109.3
C13—C12—H12119.8N6—C32—H32B109.3
C11—C12—H12119.8H32A—C32—H32B107.9
N4—Zn1—N2—C2−118.65 (18)C3—C10—C11—C12−174.7 (2)
N5—Zn1—N2—C2106.10 (18)C10—C11—C12—C130.2 (4)
N6—Zn1—N2—C217.5 (2)C11—C12—C13—C14−0.8 (4)
N4—Zn1—N2—C175.4 (2)C12—C13—C14—C150.1 (5)
N5—Zn1—N2—C1−59.8 (2)C11—C10—C15—C14−1.7 (4)
N6—Zn1—N2—C1−148.45 (19)C3—C10—C15—C14174.0 (3)
N2—Zn1—N4—C17−118.7 (2)C13—C14—C15—C101.1 (5)
N5—Zn1—N4—C1715.1 (2)C18—N3—C16—O3175.9 (3)
N6—Zn1—N4—C17111.7 (2)C18—N3—C16—N4−4.2 (3)
N2—Zn1—N4—C1663.7 (2)C17—N4—C16—O3−174.0 (3)
N5—Zn1—N4—C16−162.46 (18)Zn1—N4—C16—O34.0 (4)
N6—Zn1—N4—C16−65.9 (2)C17—N4—C16—N36.1 (3)
N4—Zn1—N5—C31120.3 (2)Zn1—N4—C16—N3−175.88 (17)
N2—Zn1—N5—C31−99.4 (2)C16—N4—C17—O4178.0 (2)
N6—Zn1—N5—C311.6 (2)Zn1—N4—C17—O40.2 (4)
N4—Zn1—N6—C32−137.5 (2)C16—N4—C17—C18−5.5 (3)
N2—Zn1—N6—C3283.8 (2)Zn1—N4—C17—C18176.76 (16)
N5—Zn1—N6—C32−24.5 (2)C16—N3—C18—C19−119.9 (2)
C3—N1—C1—O1177.2 (2)C16—N3—C18—C25111.5 (2)
C3—N1—C1—N2−4.1 (3)C16—N3—C18—C170.8 (3)
C2—N2—C1—O1177.2 (2)O4—C17—C18—N3179.6 (2)
Zn1—N2—C1—O1−15.6 (3)N4—C17—C18—N32.9 (2)
C2—N2—C1—N1−1.5 (3)O4—C17—C18—C19−62.1 (3)
Zn1—N2—C1—N1165.76 (16)N4—C17—C18—C19121.2 (2)
C1—N2—C2—O2−174.8 (2)O4—C17—C18—C2563.0 (3)
Zn1—N2—C2—O216.6 (4)N4—C17—C18—C25−113.7 (2)
C1—N2—C2—C36.1 (3)N3—C18—C19—C24132.8 (2)
Zn1—N2—C2—C3−162.49 (15)C25—C18—C19—C24−99.0 (3)
C1—N1—C3—C10121.6 (2)C17—C18—C19—C2421.6 (3)
C1—N1—C3—C4−108.2 (2)N3—C18—C19—C20−47.8 (3)
C1—N1—C3—C27.1 (3)C25—C18—C19—C2080.4 (3)
O2—C2—C3—N1173.0 (2)C17—C18—C19—C20−159.1 (2)
N2—C2—C3—N1−7.9 (2)C24—C19—C20—C21−1.9 (5)
O2—C2—C3—C1055.4 (3)C18—C19—C20—C21178.7 (3)
N2—C2—C3—C10−125.5 (2)C19—C20—C21—C22−0.9 (6)
O2—C2—C3—C4−69.8 (3)C20—C21—C22—C232.2 (7)
N2—C2—C3—C4109.3 (2)C21—C22—C23—C24−0.8 (6)
N1—C3—C4—C5−32.8 (3)C20—C19—C24—C233.4 (4)
C10—C3—C4—C596.7 (3)C18—C19—C24—C23−177.2 (2)
C2—C3—C4—C5−141.3 (2)C22—C23—C24—C19−2.1 (5)
N1—C3—C4—C9146.4 (2)N3—C18—C25—C30160.6 (2)
C10—C3—C4—C9−84.1 (3)C19—C18—C25—C3033.1 (3)
C2—C3—C4—C937.8 (3)C17—C18—C25—C30−92.6 (3)
C9—C4—C5—C60.3 (4)N3—C18—C25—C26−26.0 (3)
C3—C4—C5—C6179.5 (2)C19—C18—C25—C26−153.5 (2)
C4—C5—C6—C7−0.8 (4)C17—C18—C25—C2680.9 (3)
C5—C6—C7—C80.4 (4)C30—C25—C26—C270.2 (4)
C6—C7—C8—C90.5 (4)C18—C25—C26—C27−173.4 (3)
C7—C8—C9—C4−1.0 (4)C25—C26—C27—C280.4 (5)
C5—C4—C9—C80.6 (4)C26—C27—C28—C29−0.9 (6)
C3—C4—C9—C8−178.6 (2)C27—C28—C29—C300.8 (6)
N1—C3—C10—C15155.5 (2)C26—C25—C30—C29−0.4 (5)
C4—C3—C10—C1526.3 (3)C18—C25—C30—C29173.2 (3)
C2—C3—C10—C15−96.1 (3)C28—C29—C30—C25−0.1 (6)
N1—C3—C10—C11−28.9 (3)Zn1—N5—C31—C3223.6 (4)
C4—C3—C10—C11−158.1 (2)N5—C31—C32—N6−47.9 (5)
C2—C3—C10—C1179.5 (3)Zn1—N6—C32—C3145.3 (4)
C15—C10—C11—C121.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N6—H6B···O20.902.182.858 (3)132
C9—H9···O20.932.362.992 (3)125
C11—H11···N10.932.522.860 (4)102
C24—H24···O40.932.393.042 (4)127
C26—H26···N30.932.512.854 (4)102
N1—H1···O1i0.862.163.008 (3)167
N3—H3···O3ii0.862.042.843 (3)156
N5—H5A···O4iii0.901.972.855 (3)170
N5—H5B···O1iii0.902.183.003 (3)152

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2240).

References

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  • Hu, X.-L., Xu, X.-Y., Wang, D.-Q. & Xu, T.-T. (2006). Acta Cryst. E62, m1922–m1923.
  • Hu, X., Xu, X., Xu, T. & Wang, D. (2006). Acta Cryst. E62, m2221–m2223.
  • Milne, P., Ho, M. & Weaver, D. F. (1999). J. Mol. Struct. (THEOCHEM), 492, 19–28.
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  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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