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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page m1426
https://doi.org/10.1107/S160053680904313X

Bis(5,5-di­phenyl­hydantoinato-κN3)(ethyl­enedi­amine)zinc(II)

Xilan Hu,a* Xingyou Xu,b Daqi Wangc and Yu Zhanga

aHuaihai Institute of Technology, Jiangsu 222005, People's Republic of China, bHuaiyin Institute of Technology, Jiangsu 223003, People's Republic of China, and cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: huxilan@hhit.edu.cn

(Received 10 September 2009; accepted 20 October 2009; online 23 October 2009)

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[Milne, P., Ho, M. & Weaver, D. F. (1999). J. Mol. Struct. (THEOCHEM), 492, 19-28.]); Akitsu & Einaga (2005[Akitsu, T. & Einaga, Y. (2005). Acta Cryst. C61, m183-m186.]); Akitsu et al. (1997[Akitsu, T., Komorita, S., Kushi, Y., Li, C., Kanehisa, N. & Kai, Y. (1997). Bull. Chem. Soc. Jpn, 70, 821-827.]). For complexes with 5,5-diphenyl­hydantoinate, see: Hu, Xu, Wang & Xu (2006[Hu, X.-L., Xu, X.-Y., Wang, D.-Q. & Xu, T.-T. (2006). Acta Cryst. E62, m1922-m1923.]); Hu, Xu, Xu & Wang (2006[Hu, X., Xu, X., Xu, T. & Wang, D. (2006). Acta Cryst. E62, m2221-m2223.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C15H11N2O2)2(C2H8N2)]

  • Mr = 627.99

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.667, Tmax = 0.766

  • 7725 measured reflections

  • 5124 independent reflections

  • 4452 reflections with I > 2σ(I)

  • Rint = 0.017
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N6—H6B⋯O2 0.90 2.18 2.858 (3) 132
C9—H9⋯O2 0.93 2.36 2.992 (3) 125
C11—H11⋯N1 0.93 2.52 2.860 (4) 102
C24—H24⋯O4 0.93 2.39 3.042 (4) 127
C26—H26⋯N3 0.93 2.51 2.854 (4) 102
N1—H1⋯O1i 0.86 2.16 3.008 (3) 167
N3—H3⋯O3ii 0.86 2.04 2.843 (3) 156
N5—H5A⋯O4iii 0.90 1.97 2.855 (3) 170
N5—H5B⋯O1iii 0.90 2.18 3.003 (3) 152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) -x, -y+1, -z+1.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680904313X/bx2240sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904313X/bx2240Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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); Akitsu & Einaga (2005); Akitsu et al. (1997). For complexes with 5,5-diphenylhydantoinate, see: Hu, Xu, Wang & Xu (2006); Hu, Xu, Xu & Wang (2006).

Experimental top

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 top

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).

Structure description top

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.

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); Akitsu & Einaga (2005); Akitsu et al. (1997). For complexes with 5,5-diphenylhydantoinate, see: Hu, Xu, Wang & Xu (2006); Hu, Xu, Xu & Wang (2006).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] 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.
Bis(5,5-diphenylhydantoinato-κN3)(ethylenediamine)zinc(II) top
Crystal data top
[Zn(C15H11N2O2)2(C2H8N2)]Z = 2
Mr = 627.99F(000) = 652
Triclinic, P1Dx = 1.416 Mg m−3
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 mm−1
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 top
Bruker SMART CCD area-detector
diffractometer		5124 independent reflections
Radiation source: fine-focus sealed tube4452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ 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 top
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 = 1.03 w = 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 Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
[Zn(C15H11N2O2)2(C2H8N2)]γ = 93.302 (1)°
Mr = 627.99V = 1473.1 (3) Å3
Triclinic, P1Z = 2
a = 9.702 (1) ÅMo Kα radiation
b = 13.0520 (15) ŵ = 0.88 mm−1
c = 13.2930 (16) ÅT = 298 K
α = 109.114 (2)°0.50 × 0.46 × 0.32 mm
β = 109.462 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		5124 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4452 reflections with I > 2σ(I)
Tmin = 0.667, Tmax = 0.766Rint = 0.017
7725 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.089H-atom parameters constrained
S = 1.03Δρmax = 0.61 e Å−3
5124 reflectionsΔρmin = −0.45 e Å−3
388 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.

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) top
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formula[Zn(C15H11N2O2)2(C2H8N2)]
Mr627.99
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.702 (1), 13.0520 (15), 13.2930 (16)
α, β, γ (°)109.114 (2), 109.462 (2), 93.302 (1)
V (Å3)1473.1 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.88
Crystal size (mm)0.50 × 0.46 × 0.32
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.667, 0.766
No. of measured, independent and
observed [I > 2σ(I)] reflections		7725, 5124, 4452
Rint0.017
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.089, 1.03
No. of reflections5124
No. of parameters388
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.61, −0.45

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6B···O20.902.182.858 (3)132.0
C9—H9···O20.932.362.992 (3)125.0
C11—H11···N10.932.522.860 (4)102.0
C24—H24···O40.932.393.042 (4)127.0
C26—H26···N30.932.512.854 (4)102.0
N1—H1···O1i0.862.163.008 (3)166.7
N3—H3···O3ii0.862.042.843 (3)155.8
N5—H5A···O4iii0.901.972.855 (3)169.5
N5—H5B···O1iii0.902.183.003 (3)152.3
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+1.
 

Acknowledgements

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).

References

First citationAkitsu, T. & Einaga, Y. (2005). Acta Cryst. C61, m183–m186.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationAkitsu, T., Komorita, S., Kushi, Y., Li, C., Kanehisa, N. & Kai, Y. (1997). Bull. Chem. Soc. Jpn, 70, 821–827.  CrossRef CAS Web of Science Google Scholar
 First citationHu, X.-L., Xu, X.-Y., Wang, D.-Q. & Xu, T.-T. (2006). Acta Cryst. E62, m1922–m1923.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHu, X., Xu, X., Xu, T. & Wang, D. (2006). Acta Cryst. E62, m2221–m2223.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationMilne, P., Ho, M. & Weaver, D. F. (1999). J. Mol. Struct. (THEOCHEM), 492, 19–28.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page m1426
https://doi.org/10.1107/S160053680904313X
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