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 7| July 2009| Pages m729-m730

(μ-Acetato){μ-1,3-bis­[2-(2-oxido­benzyl­idene­amino)ethyl]-2-(2-oxido­phenyl)-1,3-imidazolidine}dizinc(II) ethanol disolvate dihydrate

aSchool of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041004, People's Republic of China, and bInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
*Correspondence e-mail: luliping@sxu.edu.cn

(Received 4 May 2009; accepted 1 June 2009; online 6 June 2009)

In the title binuclear compound, [Zn2(C27H27N4O3)(C2H3O2)]·2CH3CH2OH·2H2O, both Zn cations adopt distorted ZnO3N2 trigonal-bipyramidal geometries with one N atom in a axial site and one N atom in an equatorial site, arising from coordination by the N,N,N,N,O,O,O-hepta­dentate ligand and a bridging acetate ion. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the component units into a three-dimensional network. Two short C—H⋯O contacts are also seen.

Related literature

For further synthetic details, see: Sarma & Bailar (1955[Sarma, B. D. & Bailar, J. C. (1955). J. Am. Chem. Soc. 77, 5476-5480.]); Lu et al. (2007[Lu, L.-P., Lu, X.-P. & Zhu, M.-L. (2007). Acta Cryst. C63, m374-m376.]). For background information on the ligand, see: Fondo et al. (2002[Fondo, M., García-Deibe, A. M., Bermejo, M. R., Sanmartín, J. & Llamas-Saiz, A. L. (2002). J. Chem. Soc. Dalton Trans. pp. 4746-4750.]); Fondo et al. (2004[Fondo, M., García-Deibe, A. M., Corbella, M., Ribas, J., Llamas-Saiz, A., Bermejo, M. R. & Sanmartín, J. (2004). Dalton Trans. pp. 3503-3507.]); Prasant Kumar et al. (2006[Prasant Kumar, N., Guillem, A. & Debashis, R. (2006). Chem. Commun. pp. 3181-3183.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn2(C27H27N4O3)(C2H3O2)]·2CH6O·2H2O

  • Mr = 773.48

  • Triclinic, [P \overline 1]

  • a = 10.140 (3) Å

  • b = 11.540 (4) Å

  • c = 16.066 (5) Å

  • α = 91.972 (6)°

  • β = 93.944 (5)°

  • γ = 110.833 (5)°

  • V = 1749.4 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.43 mm−1

  • T = 298 K

  • 0.22 × 0.20 × 0.03 mm

Data collection
  • SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.744, Tmax = 0.958

  • 8975 measured reflections

  • 5943 independent reflections

  • 4785 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.151

  • S = 1.09

  • 5943 reflections

  • 437 parameters

  • 14 restraints

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.60 e Å−3

Table 1
Selected bond lengths (Å)

Zn1—O2 1.984 (2)
Zn1—O3 1.984 (3)
Zn1—O1 1.986 (3)
Zn1—N1 2.011 (3)
Zn1—N2 2.407 (3)
Zn2—O2 1.987 (2)
Zn2—O4 1.987 (3)
Zn2—O5 1.991 (3)
Zn2—N4 2.019 (3)
Zn2—N3 2.386 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8B⋯O7i 0.97 2.41 3.259 (8) 145
C12—H12⋯O8ii 0.98 2.52 3.482 (5) 169
O6—H6B⋯O5iii 0.85 2.06 2.804 (4) 146
O6—H6A⋯O1iii 0.88 2.05 2.896 (4) 161
O7—H7A⋯O4 0.85 2.15 2.971 (8) 162
O7—H7B⋯O1iv 0.86 2.48 3.225 (9) 145
O8—H8⋯O6 0.82 1.91 2.701 (5) 163
O9—H9⋯O8ii 0.82 2.08 2.849 (9) 157
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1; (iv) -x, -y+1, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS 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/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL/PC.

Supporting information


Comment top

In earlier studies of binuclear and tetranuclear complexes of a heptadentate Schiff base, 2-(2-hydroxyphenyl)-1,3-bis[4-(2-hydroxyphenyl)-3-azabut-3-enyl]- 1,3-imidazolidine (H3L), researchers reported attractive results, such as fixed atmospheric carbon dioxide (Fondo et al., 2002), magnetic properties (Fondo et al., 2004; Prasant Kumar et al., 2006). As part of our own work, the title complex, (I), has been syhtheszed in order to study its inhibiting activity on protein tyrosine phosphatase 1B (PTP1B), and its crystal structure is presented here.

The Zn—N and Zn—O distances and bond anges around two metal ions are in the normal range (Table 1). The molecular structure is illustrated in Fig. 1. Binuclear phenolic Schiff base complex (I) consists of Zn2L(OOCCH3) units with ethanol and water as solvates. Each zinc atom is coordinated by two N atoms and three O atoms from the heptadentate Schiff base ligand and an acetate. The intermetallic separation is 3.229 (2) Å shorter than that in Zn2L(OOCCH3).methanol.2H2O (Fondo et al., 2002). Two zinc ions are linked by dibridges with one phenol oxygen atom of the ligand and another bidentate acetate group.

Related literature top

For further synthetic details, see: Sarma & Bailar (1955); Lu et al. (2007). For background information on the ligand, see: Fondo et al. (2002); Fondo et al. (2004); Prasant Kumar et al. (2006).

Experimental top

The heptadentate Schiff base has been prepared following a modified literature procedure (Sarma & Bailar, 1955; Lu, et al. 2007). The ligand was collected by filtration and recrystallized from warm ethanol. Compared IR spectroscopic data with the literature values has checked identity and purity of the ligand. The title compound (I) was synthesized as following. 0.0885 g Zn(CH3CH2O)2.2H2O was added to 0.0548 g H3L in 25 ml of ethanol solution with stirring, in a 1:1 molar ratio. Refluxed for 2 h, adjusted pH 8 with 1 M NaOH after the solution cooled to room temperature, filtered. Colourless blocks of (I) were grown from the filtrate by slow evaporation.

Refinement top

H atoms attached to C atoms and O(ethanol) of (I) were placed in geometrically idealized positions, with Csp2—H = 0.93, Csp3H(methylene) = 0.97, Csp3H(methyl) = 0.96, Csp3—H = 0.98, O—H = 0.82 Å and refined with Uiso(H)=1.2Ueq or 1.5Ueq(methyl, ethanol). The water H atoms were located in a difference map and refined as riding in their as-found relative positions.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 30% probability level for Non-H atoms.
(µ-Acetato){µ-1,3-bis[2-(2-oxidobenzylideneamino)ethyl]-2-(2-oxidophenyl)- 1,3-imidazolidine}dizinc(II) ethanol disolvate dihydrate top
Crystal data top
[Zn2(C27H27N4O3)(C2H3O2)]·2CH6O·2H2OZ = 2
Mr = 773.48F(000) = 808
Triclinic, P1Dx = 1.468 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.140 (3) ÅCell parameters from 4728 reflections
b = 11.540 (4) Åθ = 2.2–26.5°
c = 16.066 (5) ŵ = 1.43 mm1
α = 91.972 (6)°T = 298 K
β = 93.944 (5)°Block, colourless
γ = 110.833 (5)°0.22 × 0.20 × 0.03 mm
V = 1749.4 (10) Å3
Data collection top
SMART 1K CCD
diffractometer
5943 independent reflections
Radiation source: fine-focus sealed tube4785 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS;Bruker, 2000)
h = 1211
Tmin = 0.744, Tmax = 0.958k = 1310
8975 measured reflectionsl = 1917
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0929P)2 + 0.4983P]
where P = (Fo2 + 2Fc2)/3
5943 reflections(Δ/σ)max = 0.009
437 parametersΔρmax = 0.82 e Å3
14 restraintsΔρmin = 0.60 e Å3
Crystal data top
[Zn2(C27H27N4O3)(C2H3O2)]·2CH6O·2H2Oγ = 110.833 (5)°
Mr = 773.48V = 1749.4 (10) Å3
Triclinic, P1Z = 2
a = 10.140 (3) ÅMo Kα radiation
b = 11.540 (4) ŵ = 1.43 mm1
c = 16.066 (5) ÅT = 298 K
α = 91.972 (6)°0.22 × 0.20 × 0.03 mm
β = 93.944 (5)°
Data collection top
SMART 1K CCD
diffractometer
5943 independent reflections
Absorption correction: multi-scan
(SADABS;Bruker, 2000)
4785 reflections with I > 2σ(I)
Tmin = 0.744, Tmax = 0.958Rint = 0.018
8975 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04514 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.09Δρmax = 0.82 e Å3
5943 reflectionsΔρmin = 0.60 e Å3
437 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
Zn10.08495 (4)0.22680 (4)0.14633 (3)0.05247 (17)
Zn20.20169 (5)0.50951 (4)0.22548 (3)0.05443 (17)
N10.0865 (3)0.0549 (3)0.1233 (2)0.0569 (8)
N20.3245 (3)0.2542 (3)0.1953 (2)0.0536 (7)
N30.4056 (3)0.4539 (3)0.2503 (2)0.0566 (8)
N40.3384 (3)0.6668 (3)0.2863 (2)0.0618 (8)
C10.2122 (4)0.0545 (4)0.1133 (2)0.0597 (10)
C20.3590 (4)0.0315 (4)0.1036 (3)0.0719 (12)
H20.38980.09830.10700.086*
C30.4571 (5)0.0861 (5)0.0895 (3)0.0774 (13)
H30.55280.09750.08380.093*
C40.4167 (5)0.1883 (5)0.0836 (3)0.0751 (12)
H40.48390.26820.07520.090*
C50.2739 (5)0.1683 (4)0.0907 (3)0.0692 (11)
H50.24550.23640.08610.083*
C60.1709 (4)0.0504 (3)0.1043 (2)0.0544 (9)
C70.0231 (4)0.0419 (4)0.1092 (2)0.0566 (9)
H70.00800.11630.10110.068*
C80.2267 (4)0.0441 (4)0.1272 (3)0.0612 (10)
H8A0.27100.07090.07610.073*
H8B0.21750.04180.13320.073*
C90.3153 (4)0.1239 (4)0.2005 (3)0.0628 (10)
H9A0.27440.09210.25160.075*
H9B0.40980.12060.20240.075*
C100.4315 (4)0.3269 (4)0.1393 (3)0.0664 (11)
H10A0.50820.29540.13760.080*
H10B0.38820.32230.08290.080*
C110.4848 (4)0.4573 (4)0.1762 (3)0.0694 (11)
H11A0.58580.48530.19210.083*
H11B0.46700.51270.13660.083*
C120.3722 (4)0.3261 (4)0.2764 (2)0.0546 (9)
H120.45960.31640.29920.065*
C130.2647 (4)0.2889 (3)0.3391 (2)0.0520 (8)
C140.2967 (5)0.2487 (4)0.4157 (3)0.0667 (11)
H140.38540.24350.42760.080*
C150.1989 (5)0.2163 (5)0.4743 (3)0.0780 (13)
H150.22200.19060.52570.094*
C160.0674 (5)0.2222 (5)0.4565 (3)0.0785 (13)
H160.00100.19940.49580.094*
C170.0326 (4)0.2613 (4)0.3813 (3)0.0613 (10)
H170.05700.26520.37050.074*
C180.1289 (4)0.2953 (3)0.3212 (2)0.0477 (8)
C190.4876 (4)0.5472 (4)0.3184 (3)0.0697 (11)
H19A0.58460.54990.32420.084*
H19B0.44670.52350.37090.084*
C200.4862 (4)0.6744 (4)0.2993 (3)0.0731 (12)
H20A0.53510.73400.34540.088*
H20B0.53440.70170.24940.088*
C210.3042 (4)0.7583 (4)0.3131 (3)0.0612 (10)
H210.37720.82670.33920.073*
C220.1655 (4)0.7655 (4)0.3069 (2)0.0566 (9)
C230.1567 (5)0.8780 (4)0.3388 (3)0.0633 (10)
H230.23820.93910.36410.076*
C240.0333 (5)0.9001 (4)0.3339 (3)0.0696 (11)
H240.03070.97550.35450.084*
C250.0882 (5)0.8085 (4)0.2975 (3)0.0702 (11)
H250.17310.82250.29300.084*
C260.0841 (4)0.6961 (4)0.2678 (3)0.0630 (10)
H260.16770.63470.24520.076*
C270.0417 (4)0.6716 (4)0.2707 (2)0.0537 (9)
C280.1736 (4)0.4442 (5)0.0426 (3)0.0613 (10)
C290.1851 (7)0.4939 (6)0.0427 (3)0.0991 (18)
H29A0.24440.46220.07330.149*
H29B0.22590.58300.03740.149*
H29C0.09260.46840.07190.149*
O10.1248 (3)0.1685 (3)0.1286 (2)0.0772 (9)
O20.0941 (2)0.3340 (2)0.24742 (14)0.0472 (5)
O30.1323 (4)0.3318 (3)0.04947 (18)0.0733 (8)
O40.2108 (4)0.5244 (3)0.1030 (2)0.0794 (9)
O50.0387 (3)0.5631 (3)0.2420 (2)0.0691 (8)
O60.2092 (3)0.6480 (3)0.7851 (2)0.0703 (8)
H6A0.20340.71530.80900.105*
H6B0.14180.58530.79900.105*
O70.1725 (9)0.7596 (7)0.0605 (5)0.213 (4)
H7A0.20310.70190.07180.320*
H7B0.20010.78600.01280.320*
C300.2098 (9)0.5605 (8)0.5762 (4)0.127 (3)
H30A0.22340.48440.59050.153*
H30B0.11170.55020.58170.153*
C310.2435 (14)0.5870 (10)0.4942 (5)0.199 (6)
H31A0.18940.63340.47100.299*
H31B0.22150.51070.46090.299*
H31C0.34270.63500.49440.299*
O80.3030 (4)0.6641 (5)0.6310 (3)0.1170 (15)
H80.28530.65090.67960.175*
C320.6498 (10)0.0359 (9)0.4137 (6)0.139 (3)
H32A0.61570.04670.43420.167*
H32B0.73380.08790.44820.167*
C330.6737 (12)0.0333 (9)0.3300 (7)0.185 (5)
H33A0.62410.04890.30490.278*
H33B0.77330.05570.32490.278*
H33C0.64020.09110.30220.278*
O90.5470 (10)0.0873 (7)0.4090 (7)0.232 (4)
H90.58420.16320.41120.349*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0555 (3)0.0558 (3)0.0513 (3)0.0263 (2)0.00372 (19)0.00521 (19)
Zn20.0532 (3)0.0547 (3)0.0556 (3)0.0197 (2)0.00390 (19)0.00497 (19)
N10.0601 (19)0.065 (2)0.0561 (18)0.0347 (17)0.0064 (15)0.0058 (15)
N20.0495 (17)0.0658 (19)0.0560 (18)0.0310 (15)0.0136 (14)0.0149 (15)
N30.0444 (16)0.064 (2)0.065 (2)0.0221 (15)0.0084 (14)0.0114 (15)
N40.0450 (17)0.067 (2)0.070 (2)0.0161 (15)0.0042 (15)0.0061 (17)
C10.055 (2)0.068 (3)0.058 (2)0.027 (2)0.0006 (18)0.0042 (19)
C20.054 (2)0.071 (3)0.090 (3)0.025 (2)0.003 (2)0.010 (2)
C30.058 (3)0.094 (4)0.081 (3)0.028 (2)0.006 (2)0.001 (3)
C40.068 (3)0.072 (3)0.071 (3)0.007 (2)0.002 (2)0.003 (2)
C50.081 (3)0.058 (2)0.070 (3)0.026 (2)0.002 (2)0.006 (2)
C60.061 (2)0.055 (2)0.049 (2)0.0223 (18)0.0014 (17)0.0055 (16)
C70.064 (2)0.052 (2)0.062 (2)0.0295 (19)0.0052 (18)0.0042 (17)
C80.059 (2)0.066 (2)0.070 (3)0.036 (2)0.0111 (19)0.004 (2)
C90.057 (2)0.079 (3)0.069 (2)0.043 (2)0.0110 (19)0.018 (2)
C100.053 (2)0.086 (3)0.069 (3)0.032 (2)0.0218 (19)0.017 (2)
C110.050 (2)0.079 (3)0.083 (3)0.023 (2)0.022 (2)0.020 (2)
C120.0420 (18)0.074 (2)0.052 (2)0.0271 (17)0.0007 (15)0.0081 (18)
C130.051 (2)0.060 (2)0.051 (2)0.0270 (17)0.0050 (16)0.0091 (16)
C140.060 (2)0.090 (3)0.059 (2)0.039 (2)0.0000 (19)0.013 (2)
C150.090 (3)0.101 (4)0.052 (2)0.044 (3)0.007 (2)0.023 (2)
C160.081 (3)0.105 (4)0.059 (3)0.040 (3)0.026 (2)0.024 (2)
C170.050 (2)0.077 (3)0.061 (2)0.0260 (19)0.0149 (18)0.010 (2)
C180.0456 (18)0.055 (2)0.0439 (18)0.0192 (16)0.0037 (14)0.0028 (15)
C190.041 (2)0.079 (3)0.083 (3)0.0179 (19)0.0087 (19)0.003 (2)
C200.048 (2)0.068 (3)0.095 (3)0.0106 (19)0.006 (2)0.003 (2)
C210.053 (2)0.055 (2)0.070 (3)0.0144 (18)0.0028 (19)0.0009 (19)
C220.059 (2)0.051 (2)0.059 (2)0.0181 (17)0.0044 (17)0.0121 (17)
C230.066 (2)0.055 (2)0.065 (2)0.0166 (19)0.0029 (19)0.0028 (18)
C240.086 (3)0.055 (2)0.074 (3)0.031 (2)0.020 (2)0.010 (2)
C250.068 (3)0.076 (3)0.074 (3)0.034 (2)0.014 (2)0.010 (2)
C260.054 (2)0.062 (2)0.070 (3)0.0180 (18)0.0047 (19)0.0014 (19)
C270.054 (2)0.053 (2)0.055 (2)0.0200 (17)0.0063 (16)0.0032 (17)
C280.061 (2)0.085 (3)0.053 (2)0.042 (2)0.0157 (18)0.017 (2)
C290.140 (5)0.107 (4)0.064 (3)0.057 (4)0.021 (3)0.029 (3)
O10.0533 (16)0.0614 (18)0.116 (3)0.0245 (14)0.0111 (16)0.0170 (17)
O20.0396 (12)0.0561 (14)0.0486 (13)0.0202 (10)0.0035 (10)0.0065 (10)
O30.097 (2)0.075 (2)0.0534 (16)0.0353 (17)0.0087 (15)0.0175 (14)
O40.110 (3)0.076 (2)0.0631 (19)0.0431 (19)0.0184 (17)0.0240 (16)
O50.0545 (15)0.0592 (17)0.090 (2)0.0205 (13)0.0054 (14)0.0136 (15)
O60.0563 (16)0.0773 (19)0.080 (2)0.0279 (14)0.0070 (14)0.0029 (15)
O70.290 (10)0.149 (6)0.199 (8)0.087 (6)0.036 (7)0.008 (5)
C300.158 (7)0.158 (7)0.089 (4)0.090 (6)0.008 (4)0.005 (4)
C310.296 (15)0.171 (9)0.074 (5)0.011 (9)0.045 (6)0.008 (5)
O80.094 (3)0.174 (4)0.076 (2)0.044 (3)0.002 (2)0.012 (3)
C320.139 (3)0.139 (3)0.139 (3)0.0500 (13)0.0112 (10)0.0098 (10)
C330.205 (11)0.136 (7)0.158 (9)0.014 (7)0.053 (8)0.001 (6)
O90.232 (4)0.232 (4)0.233 (4)0.0837 (17)0.0205 (11)0.0152 (11)
Geometric parameters (Å, º) top
Zn1—O21.984 (2)C15—H150.9300
Zn1—O31.984 (3)C16—C171.370 (6)
Zn1—O11.986 (3)C16—H160.9300
Zn1—N12.011 (3)C17—C181.387 (5)
Zn1—N22.407 (3)C17—H170.9300
Zn2—O21.987 (2)C18—O21.350 (4)
Zn2—O41.987 (3)C19—C201.515 (7)
Zn2—O51.991 (3)C19—H19A0.9700
Zn2—N42.019 (3)C19—H19B0.9700
Zn2—N32.386 (3)C20—H20A0.9700
N1—C71.265 (5)C20—H20B0.9700
N1—C81.468 (5)C21—C221.435 (6)
N2—C121.474 (5)C21—H210.9300
N2—C91.479 (5)C22—C271.406 (5)
N2—C101.493 (5)C22—C231.414 (6)
N3—C121.474 (5)C23—C241.361 (6)
N3—C111.476 (5)C23—H230.9300
N3—C191.485 (5)C24—C251.381 (7)
N4—C211.292 (5)C24—H240.9300
N4—C201.469 (5)C25—C261.382 (6)
C1—O11.302 (5)C25—H250.9300
C1—C21.412 (6)C26—C271.400 (6)
C1—C61.421 (5)C26—H260.9300
C2—C31.368 (7)C27—O51.308 (5)
C2—H20.9300C28—O31.225 (5)
C3—C41.381 (7)C28—O41.256 (5)
C3—H30.9300C28—C291.500 (6)
C4—C51.378 (7)C29—H29A0.9600
C4—H40.9300C29—H29B0.9600
C5—C61.389 (6)C29—H29C0.9600
C5—H50.9300O6—H6A0.8774
C6—C71.463 (5)O6—H6B0.8491
C7—H70.9300O7—H7A0.8487
C8—C91.495 (6)O7—H7B0.8620
C8—H8A0.9700C30—C311.400 (10)
C8—H8B0.9700C30—O81.452 (9)
C9—H9A0.9700C30—H30A0.9700
C9—H9B0.9700C30—H30B0.9700
C10—C111.491 (7)C31—H31A0.9600
C10—H10A0.9700C31—H31B0.9600
C10—H10B0.9700C31—H31C0.9600
C11—H11A0.9700O8—H80.8200
C11—H11B0.9700C32—O91.370 (11)
C12—C131.496 (5)C32—C331.383 (12)
C12—H120.9800C32—H32A0.9700
C13—C141.387 (5)C32—H32B0.9700
C13—C181.415 (5)C33—H33A0.9600
C14—C151.378 (6)C33—H33B0.9600
C14—H140.9300C33—H33C0.9600
C15—C161.370 (7)O9—H90.8200
O2—Zn1—O3108.98 (12)C15—C14—C13120.9 (4)
O2—Zn1—O193.56 (11)C15—C14—H14119.5
O3—Zn1—O198.80 (15)C13—C14—H14119.5
O2—Zn1—N1135.96 (11)C16—C15—C14119.7 (4)
O3—Zn1—N1113.08 (13)C16—C15—H15120.1
O1—Zn1—N192.47 (13)C14—C15—H15120.1
O2—Zn1—N284.15 (10)C17—C16—C15120.7 (4)
O3—Zn1—N296.71 (12)C17—C16—H16119.6
O1—Zn1—N2164.21 (13)C15—C16—H16119.6
N1—Zn1—N278.67 (12)C16—C17—C18121.0 (4)
O2—Zn2—O4109.20 (12)C16—C17—H17119.5
O2—Zn2—O593.41 (11)C18—C17—H17119.5
O4—Zn2—O599.82 (14)O2—C18—C17120.8 (3)
O2—Zn2—N4139.65 (12)O2—C18—C13120.7 (3)
O4—Zn2—N4109.35 (14)C17—C18—C13118.6 (3)
O5—Zn2—N491.40 (13)N3—C19—C20110.2 (4)
O2—Zn2—N384.67 (10)N3—C19—H19A109.6
O4—Zn2—N397.01 (13)C20—C19—H19A109.6
O5—Zn2—N3162.73 (13)N3—C19—H19B109.6
N4—Zn2—N379.32 (13)C20—C19—H19B109.6
C7—N1—C8119.3 (3)H19A—C19—H19B108.1
C7—N1—Zn1124.7 (3)N4—C20—C19108.8 (3)
C8—N1—Zn1115.9 (3)N4—C20—H20A109.9
C12—N2—C9112.3 (3)C19—C20—H20A109.9
C12—N2—C10103.0 (3)N4—C20—H20B109.9
C9—N2—C10113.8 (3)C19—C20—H20B109.9
C12—N2—Zn1113.4 (2)H20A—C20—H20B108.3
C9—N2—Zn1101.4 (2)N4—C21—C22126.8 (4)
C10—N2—Zn1113.3 (2)N4—C21—H21116.6
C12—N3—C11103.6 (3)C22—C21—H21116.6
C12—N3—C19111.6 (3)C27—C22—C23118.9 (4)
C11—N3—C19113.1 (3)C27—C22—C21125.2 (4)
C12—N3—Zn2113.5 (2)C23—C22—C21115.9 (4)
C11—N3—Zn2114.1 (2)C24—C23—C22122.4 (4)
C19—N3—Zn2101.3 (2)C24—C23—H23118.8
C21—N4—C20119.6 (4)C22—C23—H23118.8
C21—N4—Zn2124.6 (3)C23—C24—C25118.7 (4)
C20—N4—Zn2115.8 (3)C23—C24—H24120.6
O1—C1—C2118.7 (4)C25—C24—H24120.6
O1—C1—C6124.7 (4)C24—C25—C26120.4 (4)
C2—C1—C6116.6 (4)C24—C25—H25119.8
C3—C2—C1121.9 (4)C26—C25—H25119.8
C3—C2—H2119.1C25—C26—C27122.1 (4)
C1—C2—H2119.1C25—C26—H26118.9
C2—C3—C4121.3 (4)C27—C26—H26118.9
C2—C3—H3119.4O5—C27—C26119.3 (4)
C4—C3—H3119.4O5—C27—C22123.3 (3)
C5—C4—C3118.1 (4)C26—C27—C22117.4 (4)
C5—C4—H4121.0O3—C28—O4124.7 (4)
C3—C4—H4121.0O3—C28—C29119.7 (4)
C4—C5—C6122.4 (4)O4—C28—C29115.7 (4)
C4—C5—H5118.8C28—C29—H29A109.5
C6—C5—H5118.8C28—C29—H29B109.5
C5—C6—C1119.6 (4)H29A—C29—H29B109.5
C5—C6—C7116.9 (4)C28—C29—H29C109.5
C1—C6—C7123.4 (3)H29A—C29—H29C109.5
N1—C7—C6127.4 (3)H29B—C29—H29C109.5
N1—C7—H7116.3C1—O1—Zn1127.1 (3)
C6—C7—H7116.3C18—O2—Zn1116.5 (2)
N1—C8—C9108.4 (3)C18—O2—Zn2116.3 (2)
N1—C8—H8A110.0Zn1—O2—Zn2108.80 (11)
C9—C8—H8A110.0C28—O3—Zn1133.2 (3)
N1—C8—H8B110.0C28—O4—Zn2131.8 (3)
C9—C8—H8B110.0C27—O5—Zn2128.0 (2)
H8A—C8—H8B108.4H6A—O6—H6B108.8
N2—C9—C8111.1 (3)H7A—O7—H7B108.3
N2—C9—H9A109.4C31—C30—O8107.5 (8)
C8—C9—H9A109.4C31—C30—H30A110.2
N2—C9—H9B109.4O8—C30—H30A110.2
C8—C9—H9B109.4C31—C30—H30B110.2
H9A—C9—H9B108.0O8—C30—H30B110.2
C11—C10—N2105.4 (3)H30A—C30—H30B108.5
C11—C10—H10A110.7C30—C31—H31A109.5
N2—C10—H10A110.7C30—C31—H31B109.5
C11—C10—H10B110.7H31A—C31—H31B109.5
N2—C10—H10B110.7C30—C31—H31C109.5
H10A—C10—H10B108.8H31A—C31—H31C109.5
N3—C11—C10105.2 (3)H31B—C31—H31C109.5
N3—C11—H11A110.7C30—O8—H8109.5
C10—C11—H11A110.7O9—C32—C3399.1 (10)
N3—C11—H11B110.7O9—C32—H32A111.9
C10—C11—H11B110.7C33—C32—H32A111.9
H11A—C11—H11B108.8O9—C32—H32B111.9
N3—C12—N2101.1 (3)C33—C32—H32B112.0
N3—C12—C13114.4 (3)H32A—C32—H32B109.6
N2—C12—C13113.5 (3)C32—C33—H33A109.5
N3—C12—H12109.2C32—C33—H33B109.5
N2—C12—H12109.2H33A—C33—H33B109.5
C13—C12—H12109.2C32—C33—H33C109.5
C14—C13—C18119.1 (3)H33A—C33—H33C109.5
C14—C13—C12120.7 (3)H33B—C33—H33C109.5
C18—C13—C12120.2 (3)C32—O9—H9109.5
O2—Zn1—N1—C794.1 (3)N3—C12—C13—C14122.5 (4)
O3—Zn1—N1—C7104.3 (3)N2—C12—C13—C14122.1 (4)
O1—Zn1—N1—C73.6 (3)N3—C12—C13—C1857.0 (5)
N2—Zn1—N1—C7163.2 (3)N2—C12—C13—C1858.4 (5)
O2—Zn1—N1—C883.2 (3)C18—C13—C14—C150.7 (7)
O3—Zn1—N1—C878.5 (3)C12—C13—C14—C15178.9 (4)
O1—Zn1—N1—C8179.1 (3)C13—C14—C15—C160.9 (8)
N2—Zn1—N1—C814.1 (3)C14—C15—C16—C170.8 (8)
O2—Zn1—N2—C123.6 (2)C15—C16—C17—C180.4 (8)
O3—Zn1—N2—C12112.1 (3)C16—C17—C18—O2179.9 (4)
O1—Zn1—N2—C1278.7 (5)C16—C17—C18—C130.1 (6)
N1—Zn1—N2—C12135.6 (3)C14—C13—C18—O2180.0 (4)
O2—Zn1—N2—C9124.3 (2)C12—C13—C18—O20.4 (5)
O3—Zn1—N2—C9127.2 (2)C14—C13—C18—C170.3 (6)
O1—Zn1—N2—C941.9 (5)C12—C13—C18—C17179.3 (4)
N1—Zn1—N2—C915.0 (2)C12—N3—C19—C20164.7 (3)
O2—Zn1—N2—C10113.3 (3)C11—N3—C19—C2078.9 (4)
O3—Zn1—N2—C104.8 (3)Zn2—N3—C19—C2043.7 (4)
O1—Zn1—N2—C10164.3 (4)C21—N4—C20—C19142.6 (4)
N1—Zn1—N2—C10107.5 (3)Zn2—N4—C20—C1937.8 (5)
O2—Zn2—N3—C124.4 (2)N3—C19—C20—N456.2 (5)
O4—Zn2—N3—C12113.1 (3)C20—N4—C21—C22179.0 (4)
O5—Zn2—N3—C1279.9 (5)Zn2—N4—C21—C221.4 (6)
N4—Zn2—N3—C12138.4 (3)N4—C21—C22—C270.7 (7)
O2—Zn2—N3—C11114.0 (3)N4—C21—C22—C23177.9 (4)
O4—Zn2—N3—C115.3 (3)C27—C22—C23—C241.7 (6)
O5—Zn2—N3—C11161.7 (4)C21—C22—C23—C24177.0 (4)
N4—Zn2—N3—C11103.2 (3)C22—C23—C24—C251.1 (7)
O2—Zn2—N3—C19124.1 (3)C23—C24—C25—C260.8 (7)
O4—Zn2—N3—C19127.2 (3)C24—C25—C26—C272.0 (7)
O5—Zn2—N3—C1939.8 (5)C25—C26—C27—O5179.6 (4)
N4—Zn2—N3—C1918.7 (3)C25—C26—C27—C221.3 (6)
O2—Zn2—N4—C21101.8 (4)C23—C22—C27—O5177.7 (4)
O4—Zn2—N4—C2196.1 (4)C21—C22—C27—O53.6 (6)
O5—Zn2—N4—C214.9 (4)C23—C22—C27—C260.5 (6)
N3—Zn2—N4—C21170.2 (4)C21—C22—C27—C26178.1 (4)
O2—Zn2—N4—C2078.5 (3)C2—C1—O1—Zn1179.1 (3)
O4—Zn2—N4—C2083.6 (3)C6—C1—O1—Zn11.6 (6)
O5—Zn2—N4—C20175.5 (3)O2—Zn1—O1—C1132.8 (4)
N3—Zn2—N4—C2010.2 (3)O3—Zn1—O1—C1117.4 (4)
O1—C1—C2—C3178.3 (5)N1—Zn1—O1—C13.6 (4)
C6—C1—C2—C32.4 (7)N2—Zn1—O1—C151.7 (7)
C1—C2—C3—C40.3 (8)C17—C18—O2—Zn1114.9 (3)
C2—C3—C4—C51.3 (7)C13—C18—O2—Zn165.3 (4)
C3—C4—C5—C60.8 (7)C17—C18—O2—Zn2114.7 (3)
C4—C5—C6—C11.3 (6)C13—C18—O2—Zn265.0 (4)
C4—C5—C6—C7179.0 (4)O3—Zn1—O2—C18150.8 (2)
O1—C1—C6—C5177.9 (4)O1—Zn1—O2—C18108.6 (2)
C2—C1—C6—C52.8 (6)N1—Zn1—O2—C1811.3 (3)
O1—C1—C6—C71.7 (6)N2—Zn1—O2—C1855.7 (2)
C2—C1—C6—C7177.6 (4)O3—Zn1—O2—Zn217.05 (15)
C8—N1—C7—C6179.0 (4)O1—Zn1—O2—Zn2117.62 (13)
Zn1—N1—C7—C61.8 (6)N1—Zn1—O2—Zn2145.11 (15)
C5—C6—C7—N1178.0 (4)N2—Zn1—O2—Zn278.06 (11)
C1—C6—C7—N11.6 (6)O4—Zn2—O2—C18151.3 (2)
C7—N1—C8—C9135.9 (4)O5—Zn2—O2—C18107.1 (2)
Zn1—N1—C8—C941.5 (4)N4—Zn2—O2—C1810.9 (3)
C12—N2—C9—C8162.5 (3)N3—Zn2—O2—C1855.7 (2)
C10—N2—C9—C881.0 (4)O4—Zn2—O2—Zn117.41 (15)
Zn1—N2—C9—C841.1 (3)O5—Zn2—O2—Zn1119.05 (13)
N1—C8—C9—N256.5 (4)N4—Zn2—O2—Zn1144.75 (16)
C12—N2—C10—C1126.8 (4)N3—Zn2—O2—Zn178.17 (12)
C9—N2—C10—C11148.6 (3)O4—C28—O3—Zn17.9 (7)
Zn1—N2—C10—C1196.2 (3)C29—C28—O3—Zn1173.5 (4)
C12—N3—C11—C1028.0 (4)O2—Zn1—O3—C286.1 (4)
C19—N3—C11—C10149.0 (3)O1—Zn1—O3—C28103.0 (4)
Zn2—N3—C11—C1095.8 (3)N1—Zn1—O3—C28160.5 (4)
N2—C10—C11—N30.7 (4)N2—Zn1—O3—C2880.0 (4)
C11—N3—C12—N244.8 (3)O3—C28—O4—Zn27.1 (7)
C19—N3—C12—N2166.8 (3)C29—C28—O4—Zn2174.2 (4)
Zn2—N3—C12—N279.5 (3)O2—Zn2—O4—C287.3 (4)
C11—N3—C12—C13167.2 (3)O5—Zn2—O4—C28104.4 (4)
C19—N3—C12—C1370.8 (4)N4—Zn2—O4—C28160.6 (4)
Zn2—N3—C12—C1342.9 (4)N3—Zn2—O4—C2879.5 (4)
C9—N2—C12—N3166.8 (3)C26—C27—O5—Zn2172.0 (3)
C10—N2—C12—N343.9 (3)C22—C27—O5—Zn29.8 (6)
Zn1—N2—C12—N379.0 (3)O2—Zn2—O5—C27149.1 (3)
C9—N2—C12—C1370.2 (4)O4—Zn2—O5—C27100.7 (3)
C10—N2—C12—C13166.9 (3)N4—Zn2—O5—C279.2 (3)
Zn1—N2—C12—C1344.1 (4)N3—Zn2—O5—C2766.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O7i0.972.413.259 (8)145
C12—H12···O8ii0.982.523.482 (5)169
O6—H6B···O5iii0.852.062.804 (4)146
O6—H6A···O1iii0.882.052.896 (4)161
O7—H7A···O40.852.152.971 (8)162
O7—H7B···O1iv0.862.483.225 (9)145
O8—H8···O60.821.912.701 (5)163
O9—H9···O8ii0.822.082.849 (9)157
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z+1; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Zn2(C27H27N4O3)(C2H3O2)]·2CH6O·2H2O
Mr773.48
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.140 (3), 11.540 (4), 16.066 (5)
α, β, γ (°)91.972 (6), 93.944 (5), 110.833 (5)
V3)1749.4 (10)
Z2
Radiation typeMo Kα
µ (mm1)1.43
Crystal size (mm)0.22 × 0.20 × 0.03
Data collection
DiffractometerSMART 1K CCD
diffractometer
Absorption correctionMulti-scan
(SADABS;Bruker, 2000)
Tmin, Tmax0.744, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
8975, 5943, 4785
Rint0.018
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.151, 1.09
No. of reflections5943
No. of parameters437
No. of restraints14
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 0.60

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Selected bond lengths (Å) top
Zn1—O21.984 (2)Zn2—O21.987 (2)
Zn1—O31.984 (3)Zn2—O41.987 (3)
Zn1—O11.986 (3)Zn2—O51.991 (3)
Zn1—N12.011 (3)Zn2—N42.019 (3)
Zn1—N22.407 (3)Zn2—N32.386 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O7i0.972.413.259 (8)145
C12—H12···O8ii0.982.523.482 (5)169
O6—H6B···O5iii0.852.062.804 (4)146
O6—H6A···O1iii0.882.052.896 (4)161
O7—H7A···O40.852.152.971 (8)162
O7—H7B···O1iv0.862.483.225 (9)145
O8—H8···O60.821.912.701 (5)163
O9—H9···O8ii0.822.082.849 (9)157
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z+1; (iv) x, y+1, z.
 

Acknowledgements

The authors acknowledge the National and Shanxi Provincial Natural Science Foundation of China (grant Nos. 20471033 and 20051013) as well as the Overseas Returned Scholar Foundation of Shanxi Province of China in 2008 for financial support.

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFondo, M., García-Deibe, A. M., Bermejo, M. R., Sanmartín, J. & Llamas-Saiz, A. L. (2002). J. Chem. Soc. Dalton Trans. pp. 4746–4750.  Web of Science CSD CrossRef Google Scholar
First citationFondo, M., García-Deibe, A. M., Corbella, M., Ribas, J., Llamas-Saiz, A., Bermejo, M. R. & Sanmartín, J. (2004). Dalton Trans. pp. 3503–3507.  Web of Science CSD CrossRef PubMed Google Scholar
First citationLu, L.-P., Lu, X.-P. & Zhu, M.-L. (2007). Acta Cryst. C63, m374–m376.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationPrasant Kumar, N., Guillem, A. & Debashis, R. (2006). Chem. Commun. pp. 3181–3183.  Google Scholar
First citationSarma, B. D. & Bailar, J. C. (1955). J. Am. Chem. Soc. 77, 5476–5480.  CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 7| July 2009| Pages m729-m730
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