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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m985.
Published online 2009 July 25. doi:  10.1107/S1600536809028530
PMCID: PMC2977276

[μ-14,29-Di-tert-butyl-3,10,18,25-tetra­azatpenta­cyclo­[25.3.1.112,16.04,9.019,24]dotriaconta-1(31),4,6,8,12(32),14,16,19,21,23,27,29-dodeca­ene-31,32-diol­ato]bis­[(nitrato-κ2 O,O′)zinc(II)]

Abstract

In the title centrosymmetric dinuclear zinc(II) complex, [Zn2(C36H42N4O2)(NO3)2], the ZnII atom has a distorted octa­hedral geometry, defined by two N atoms and two O atoms from the macrocyclic ligand and two O atoms from a chelating nitrate anion and are bridged by two phenolate O atoms, forming a four-membered Zn2O2 ring.

Related literature

For general background to the biochemistry of zinc(II) compounds, see: Bazzicalupi et al. (1997 [triangle]); Burley et al. (1990 [triangle]); Lipscomb & Straeter (1996 [triangle]); Roderick & Mathews (1993 [triangle]). For related structures, see: Dutta et al. (2005 [triangle]). For further synthetic details, see: Fan et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m985-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C36H42N4O2)(NO3)2]
  • M r = 817.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m985-efi1.jpg
  • a = 13.7149 (8) Å
  • b = 18.0691 (10) Å
  • c = 7.3523 (3) Å
  • β = 101.110 (5)°
  • V = 1787.87 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.40 mm−1
  • T = 293 K
  • 0.45 × 0.25 × 0.20 mm

Data collection

  • Oxford Diffraction Gemini R Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.661, T max = 0.752
  • 15034 measured reflections
  • 4340 independent reflections
  • 1698 reflections with I > 2σ(I)
  • R int = 0.099

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.065
  • S = 0.91
  • 4340 reflections
  • 241 parameters
  • 357 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); data reduction: CrysAlis RED; 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 bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028530/hy2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028530/hy2213Isup2.hkl

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

Acknowledgments

We thank the National Natural Science Foundation of China (grant No. 20471014), the Program for New Century Excellent Talents in Chinese Universities (grant No. NCET-05–0320), the Fok Ying Tung Education Foundation and the Analysis and Testing Foundation of Northeast Normal University for support.

supplementary crystallographic information

Comment

Dinuclear zinc(II) compounds have attracted much interest as a result of their significance in biological systems (Burley et al., 1990; Roderick & Mathews, 1993). In addition, some synthetic dinuclear zinc(II) compounds are found to have functions in dephosphorylation (Bazzicalupi et al., 1997). As part of our studies in this area, the title compound, a new dinuclear zinc(II) compound, has been synthesized and its structure is reported here (Fig. 1).

In the title centrosymmetric dinuclear zinc(II) compound, each of the two ZnII atoms has a distorted octahedral geometry, defined by two N atoms and two O atoms from the macrocyclic (C36H42N4O2) ligand and two O atoms from a chelating nitrate anion. The two Zn atoms are bridged by two phenolate O atoms, forming a four-membered Zn2O2 ring. The Zn—O and Zn—N distances are normal (Table 1) (Dutta et al., 2005).

Experimental

The title compound was prepared by a reaction between the macrocyclic ligand C36H44N4O2 (H2L), which was synthesized according to the published procedure (Fan et al., 2009), and zinc nitrate. A mixture of H2L (0.135 g, 0.25 mmol) and Zn(NO3)2.6H2O (0.149 g, 0.5 mmol) in ethanol (20 ml) was heated with stirring to yield a clear pale yellow solution. Filtration and cooling to room temperature resulted in the formation of a crystalline precipitate. Recrystallization by slow evaporation of an ethanol solution of the compound resulted in well formed yellow blocks of the title compound (yield 52%).

Refinement

N-bonded H atoms were located in a difference map and their coordinates were freely refined, with Uiso fixed. C-bonded H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2(or 1.5 for methyl)Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound. Displaceement ellipsoids are draw at the 30% probability level. H atoms have been omitted for clarity.

Crystal data

[Zn2(C36H42N4O2)(NO3)2]F(000) = 848
Mr = 817.20Dx = 1.518 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2682 reflections
a = 13.7149 (8) Åθ = 1.9–29.2°
b = 18.0691 (10) ŵ = 1.40 mm1
c = 7.3523 (3) ÅT = 293 K
β = 101.110 (5)°Block, yellow
V = 1787.87 (16) Å30.45 × 0.25 × 0.20 mm
Z = 2

Data collection

Oxford Diffraction Gemini R Ultra diffractometer4340 independent reflections
Radiation source: fine-focus sealed tube1698 reflections with I > 2σ(I)
graphiteRint = 0.099
Detector resolution: 10.0 pixels mm-1θmax = 29.3°, θmin = 1.9°
ω scansh = −16→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −24→24
Tmin = 0.661, Tmax = 0.752l = −8→10
15034 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 0.91w = 1/[σ2(Fo2) + (0.01P)2] where P = (Fo2 + 2Fc2)/3
4340 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.66 e Å3
357 restraintsΔρmin = −0.45 e Å3

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

xyzUiso*/Ueq
C10.2727 (3)0.6078 (2)0.1435 (5)0.0401 (11)
C20.1724 (3)0.6150 (2)0.1476 (5)0.0486 (12)
H20.12540.58970.06210.058*
C30.1424 (3)0.6598 (2)0.2783 (5)0.0506 (12)
H30.07530.66510.28070.061*
C40.2122 (4)0.6965 (2)0.4047 (5)0.0469 (12)
H40.19200.72660.49310.056*
C50.3108 (3)0.6893 (2)0.4022 (5)0.0404 (11)
H50.35720.71410.49000.048*
C60.3426 (3)0.6460 (2)0.2723 (5)0.0332 (10)
C70.5006 (3)0.4041 (2)−0.4386 (4)0.0334 (11)
H7A0.49970.3731−0.54670.040*
H7B0.53820.4484−0.45370.040*
C80.3954 (3)0.4258 (2)−0.4294 (4)0.0296 (9)
C90.3152 (3)0.3961 (2)−0.5486 (5)0.0386 (10)
H90.32680.3600−0.63200.046*
C100.2177 (3)0.4175 (3)−0.5504 (5)0.0427 (10)
C110.2043 (3)0.4716 (2)−0.4249 (5)0.0464 (11)
H110.14000.4879−0.42430.056*
C120.2823 (3)0.5029 (2)−0.2995 (5)0.0375 (11)
C130.3800 (3)0.4796 (2)−0.3002 (5)0.0322 (10)
C140.2598 (3)0.5610 (3)−0.1703 (5)0.0584 (12)
H14A0.27070.6085−0.22440.070*
H14B0.18940.5578−0.16840.070*
C150.1319 (3)0.3808 (3)−0.6848 (6)0.0525 (12)
C160.1355 (4)0.2980 (3)−0.6507 (6)0.0896 (16)
H16A0.19870.2791−0.66680.134*
H16B0.08350.2744−0.73720.134*
H16C0.12670.2882−0.52660.134*
C170.1414 (3)0.3929 (2)−0.8848 (5)0.0749 (14)
H17A0.20440.3745−0.90310.112*
H17B0.13670.4448−0.91280.112*
H17C0.08890.3670−0.96530.112*
C180.0325 (3)0.4077 (3)−0.6600 (6)0.0918 (16)
H18A0.02530.3993−0.53440.138*
H18B−0.01850.3813−0.74270.138*
H18C0.02680.4596−0.68690.138*
N10.3096 (3)0.5622 (2)0.0108 (5)0.0479 (11)
N20.4476 (3)0.63682 (17)0.2695 (4)0.0315 (9)
N30.5574 (4)0.6847 (2)−0.1030 (5)0.0470 (12)
O10.6025 (2)0.63223 (18)−0.0177 (4)0.0545 (8)
O20.4639 (3)0.68288 (18)−0.1261 (4)0.0575 (10)
O30.5992 (3)0.73463 (18)−0.1672 (4)0.0714 (11)
O40.4592 (2)0.50597 (14)−0.1821 (3)0.0309 (7)
Zn10.46177 (4)0.57671 (3)0.03129 (6)0.03462 (15)
H1N0.296 (3)0.5176 (13)0.031 (5)0.052*
H2N0.475 (3)0.6800 (13)0.282 (5)0.052*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.034 (3)0.050 (3)0.040 (2)0.006 (2)0.017 (2)−0.011 (2)
C20.037 (3)0.065 (3)0.045 (2)0.003 (2)0.012 (2)−0.008 (2)
C30.038 (3)0.063 (3)0.055 (3)0.006 (2)0.019 (2)−0.010 (2)
C40.046 (3)0.052 (3)0.045 (2)0.011 (3)0.014 (2)−0.014 (2)
C50.038 (3)0.045 (3)0.039 (2)0.003 (2)0.010 (2)−0.010 (2)
C60.029 (3)0.041 (3)0.032 (2)0.009 (2)0.012 (2)0.0007 (19)
C70.036 (3)0.039 (3)0.026 (2)0.004 (2)0.0078 (19)−0.0020 (19)
C80.030 (2)0.033 (2)0.0254 (19)−0.003 (2)0.0060 (18)−0.003 (2)
C90.041 (2)0.044 (2)0.0300 (19)0.001 (2)0.0052 (19)−0.0112 (18)
C100.033 (2)0.052 (2)0.041 (2)−0.005 (2)0.0022 (18)−0.013 (2)
C110.031 (2)0.063 (3)0.043 (2)0.003 (2)0.004 (2)−0.010 (2)
C120.035 (2)0.042 (2)0.034 (2)0.004 (2)0.003 (2)−0.0104 (19)
C130.031 (2)0.038 (2)0.028 (2)0.001 (2)0.007 (2)−0.0019 (19)
C140.043 (3)0.078 (3)0.051 (2)0.020 (2)0.001 (2)−0.018 (2)
C150.034 (3)0.061 (3)0.061 (2)0.001 (2)0.006 (2)−0.019 (2)
C160.083 (3)0.087 (3)0.088 (3)−0.027 (3)−0.011 (3)−0.007 (3)
C170.064 (3)0.089 (3)0.062 (3)−0.011 (3)−0.013 (2)−0.013 (3)
C180.048 (3)0.120 (4)0.101 (3)−0.012 (3)−0.002 (3)−0.055 (3)
N10.032 (2)0.065 (3)0.046 (2)0.000 (3)0.0058 (19)−0.017 (3)
N20.037 (3)0.028 (2)0.0292 (18)0.004 (2)0.0064 (18)−0.0054 (17)
N30.071 (4)0.031 (3)0.041 (2)0.005 (3)0.018 (3)−0.005 (2)
O10.058 (2)0.046 (2)0.062 (2)−0.0080 (17)0.0188 (18)0.0047 (17)
O20.055 (3)0.063 (3)0.0534 (19)0.003 (2)0.007 (2)−0.0025 (17)
O30.098 (3)0.038 (2)0.090 (2)−0.012 (2)0.046 (2)0.0090 (19)
O40.032 (2)0.0326 (18)0.0283 (15)0.0044 (15)0.0067 (14)−0.0065 (13)
Zn10.0343 (3)0.0372 (3)0.0319 (2)0.0038 (4)0.0052 (2)−0.0047 (3)

Geometric parameters (Å, °)

C1—C21.388 (5)C14—H14A0.9700
C1—C61.393 (5)C14—H14B0.9700
C1—N11.441 (5)C15—C181.490 (5)
C2—C31.378 (5)C15—C161.516 (6)
C2—H20.9300C15—C171.517 (5)
C3—C41.369 (5)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.363 (5)C16—H16C0.9600
C4—H40.9300C17—H17A0.9600
C5—C61.368 (5)C17—H17B0.9600
C5—H50.9300C17—H17C0.9600
C6—N21.453 (5)C18—H18A0.9600
C7—N2i1.502 (4)C18—H18B0.9600
C7—C81.510 (5)C18—H18C0.9600
C7—H7A0.9700Zn1—N12.081 (4)
C7—H7B0.9700N1—H1N0.845 (19)
C8—C91.376 (5)N2—C7i1.502 (4)
C8—C131.404 (5)Zn1—N22.102 (3)
C9—C101.390 (5)N2—H2N0.863 (19)
C9—H90.9300N3—O31.212 (4)
C10—C111.380 (5)N3—O11.234 (4)
C10—C151.534 (5)N3—O21.262 (5)
C11—C121.391 (5)Zn1—O12.264 (3)
C11—H110.9300Zn1—O22.243 (3)
C12—C131.405 (5)Zn1—O42.019 (2)
C12—C141.487 (5)Zn1—O4i2.043 (2)
C13—O41.341 (4)Zn1—Zn1i3.0302 (10)
C14—N11.375 (4)
C2—C1—C6119.6 (4)C15—C16—H16C109.5
C2—C1—N1123.1 (4)H16A—C16—H16C109.5
C6—C1—N1117.3 (4)H16B—C16—H16C109.5
C3—C2—C1120.0 (4)C15—C17—H17A109.5
C3—C2—H2120.0C15—C17—H17B109.5
C1—C2—H2120.0H17A—C17—H17B109.5
C4—C3—C2119.6 (4)C15—C17—H17C109.5
C4—C3—H3120.2H17A—C17—H17C109.5
C2—C3—H3120.2H17B—C17—H17C109.5
C3—C4—C5120.7 (4)C15—C18—H18A109.5
C3—C4—H4119.7C15—C18—H18B109.5
C5—C4—H4119.7H18A—C18—H18B109.5
C4—C5—C6120.9 (4)C15—C18—H18C109.5
C4—C5—H5119.5H18A—C18—H18C109.5
C6—C5—H5119.5H18B—C18—H18C109.5
C5—C6—C1119.2 (4)C14—N1—C1119.5 (4)
C5—C6—N2121.6 (4)C14—N1—Zn1112.1 (3)
C1—C6—N2119.1 (4)C1—N1—Zn1110.9 (3)
N2i—C7—C8113.3 (3)C14—N1—H1N94 (3)
N2i—C7—H7A108.9C1—N1—H1N108 (3)
C8—C7—H7A108.9Zn1—N1—H1N111 (3)
N2i—C7—H7B108.9C6—N2—C7i110.9 (3)
C8—C7—H7B108.9C6—N2—Zn1108.8 (2)
H7A—C7—H7B107.7C7i—N2—Zn1109.3 (2)
C9—C8—C13119.6 (4)C6—N2—H2N108 (3)
C9—C8—C7121.6 (4)C7i—N2—H2N103 (3)
C13—C8—C7118.7 (4)Zn1—N2—H2N116 (3)
C8—C9—C10123.2 (4)O3—N3—O1122.8 (5)
C8—C9—H9118.4O3—N3—O2120.7 (5)
C10—C9—H9118.4O1—N3—O2116.4 (5)
C11—C10—C9116.3 (4)N3—O1—Zn193.6 (3)
C11—C10—C15123.5 (4)N3—O2—Zn193.8 (3)
C9—C10—C15120.2 (4)C13—O4—Zn1128.2 (2)
C10—C11—C12123.1 (4)C13—O4—Zn1i111.8 (2)
C10—C11—H11118.5Zn1—O4—Zn1i96.50 (9)
C12—C11—H11118.5O4—Zn1—O4i83.50 (9)
C11—C12—C13119.2 (4)O4—Zn1—N189.82 (13)
C11—C12—C14118.9 (4)O4i—Zn1—N1111.54 (13)
C13—C12—C14121.9 (4)O4—Zn1—N2169.86 (13)
O4—C13—C12123.1 (4)O4i—Zn1—N292.88 (11)
O4—C13—C8118.4 (4)N1—Zn1—N282.68 (14)
C12—C13—C8118.6 (4)O4—Zn1—O298.08 (11)
N1—C14—C12120.3 (4)O4i—Zn1—O2147.90 (13)
N1—C14—H14A107.2N1—Zn1—O2100.54 (14)
C12—C14—H14A107.2N2—Zn1—O290.02 (12)
N1—C14—H14B107.2O4—Zn1—O192.56 (11)
C12—C14—H14B107.2O4i—Zn1—O191.78 (11)
H14A—C14—H14B106.9N1—Zn1—O1156.68 (13)
C18—C15—C16107.6 (4)N2—Zn1—O197.03 (12)
C18—C15—C17108.8 (4)O2—Zn1—O156.16 (11)
C16—C15—C17107.2 (4)O4—Zn1—Zn1i42.06 (7)
C18—C15—C10112.8 (4)O4i—Zn1—Zn1i41.45 (6)
C16—C15—C10108.9 (4)N1—Zn1—Zn1i104.20 (11)
C17—C15—C10111.4 (4)N2—Zn1—Zn1i133.61 (9)
C15—C16—H16A109.5O2—Zn1—Zn1i131.67 (9)
C15—C16—H16B109.5O1—Zn1—Zn1i92.91 (9)
H16A—C16—H16B109.5
C6—C1—C2—C30.1 (6)C12—C13—O4—Zn14.7 (5)
N1—C1—C2—C3−179.9 (4)C8—C13—O4—Zn1−174.7 (2)
C1—C2—C3—C4−0.6 (6)C12—C13—O4—Zn1i122.7 (4)
C2—C3—C4—C50.2 (7)C8—C13—O4—Zn1i−56.6 (4)
C3—C4—C5—C60.8 (7)C13—O4—Zn1—O4i124.4 (3)
C4—C5—C6—C1−1.2 (6)Zn1i—O4—Zn1—O4i0.0
C4—C5—C6—N2−179.0 (4)C13—O4—Zn1—N112.7 (3)
C2—C1—C6—C50.8 (6)Zn1i—O4—Zn1—N1−111.71 (13)
N1—C1—C6—C5−179.2 (4)C13—O4—Zn1—N254.8 (8)
C2—C1—C6—N2178.7 (4)Zn1i—O4—Zn1—N2−69.6 (7)
N1—C1—C6—N2−1.4 (6)C13—O4—Zn1—O2−87.9 (3)
N2i—C7—C8—C9−114.2 (4)Zn1i—O4—Zn1—O2147.67 (13)
N2i—C7—C8—C1368.2 (5)C13—O4—Zn1—O1−144.1 (3)
C13—C8—C9—C100.9 (6)Zn1i—O4—Zn1—O191.50 (12)
C7—C8—C9—C10−176.7 (4)C13—O4—Zn1—Zn1i124.4 (3)
C8—C9—C10—C110.4 (6)C14—N1—Zn1—O4−41.6 (3)
C8—C9—C10—C15−178.8 (4)C1—N1—Zn1—O4−177.9 (3)
C9—C10—C11—C12−1.3 (6)C14—N1—Zn1—O4i−124.5 (3)
C15—C10—C11—C12177.8 (4)C1—N1—Zn1—O4i99.2 (3)
C10—C11—C12—C130.9 (6)C14—N1—Zn1—N2145.2 (3)
C10—C11—C12—C14179.8 (4)C1—N1—Zn1—N28.9 (3)
C11—C12—C13—O4−178.9 (3)C14—N1—Zn1—O256.6 (3)
C14—C12—C13—O42.2 (6)C1—N1—Zn1—O2−79.7 (3)
C11—C12—C13—C80.5 (6)C14—N1—Zn1—O154.5 (5)
C14—C12—C13—C8−178.4 (4)C1—N1—Zn1—O1−81.8 (4)
C9—C8—C13—O4178.1 (3)C14—N1—Zn1—Zn1i−81.5 (3)
C7—C8—C13—O4−4.3 (5)C1—N1—Zn1—Zn1i142.2 (2)
C9—C8—C13—C12−1.3 (6)C6—N2—Zn1—O4−51.9 (8)
C7—C8—C13—C12176.3 (3)C7i—N2—Zn1—O469.3 (8)
C11—C12—C14—N1140.1 (4)C6—N2—Zn1—O4i−120.7 (2)
C13—C12—C14—N1−40.9 (7)C7i—N2—Zn1—O4i0.5 (2)
C11—C10—C15—C18−2.3 (6)C6—N2—Zn1—N1−9.4 (2)
C9—C10—C15—C18176.8 (4)C7i—N2—Zn1—N1111.8 (3)
C11—C10—C15—C16−121.6 (5)C6—N2—Zn1—O291.3 (3)
C9—C10—C15—C1657.5 (5)C7i—N2—Zn1—O2−147.6 (2)
C11—C10—C15—C17120.4 (4)C6—N2—Zn1—O1147.1 (2)
C9—C10—C15—C17−60.5 (6)C7i—N2—Zn1—O1−91.7 (2)
C12—C14—N1—C1−166.4 (4)C6—N2—Zn1—Zn1i−112.0 (2)
C12—C14—N1—Zn161.4 (5)C7i—N2—Zn1—Zn1i9.2 (3)
C2—C1—N1—C1440.4 (6)N3—O2—Zn1—O4−88.6 (2)
C6—C1—N1—C14−139.5 (4)N3—O2—Zn1—O4i2.0 (3)
C2—C1—N1—Zn1173.0 (3)N3—O2—Zn1—N1−180.0 (2)
C6—C1—N1—Zn1−6.9 (5)N3—O2—Zn1—N297.5 (2)
C5—C6—N2—C7i66.3 (5)N3—O2—Zn1—O1−1.0 (2)
C1—C6—N2—C7i−111.5 (4)N3—O2—Zn1—Zn1i−60.0 (3)
C5—C6—N2—Zn1−173.5 (3)N3—O1—Zn1—O499.0 (2)
C1—C6—N2—Zn18.7 (4)N3—O1—Zn1—O4i−177.4 (2)
O3—N3—O1—Zn1−179.5 (4)N3—O1—Zn1—N13.5 (5)
O2—N3—O1—Zn1−1.7 (4)N3—O1—Zn1—N2−84.3 (2)
O3—N3—O2—Zn1179.5 (3)N3—O1—Zn1—O21.0 (2)
O1—N3—O2—Zn11.7 (4)N3—O1—Zn1—Zn1i141.1 (2)

Symmetry codes: (i) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2213).

References

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