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

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ISSN: 2056-9890

Bis[methyl 3-(propyl­amino)­but-2-eno­ato]zinc

aHoward University, Department of Chemistry, 525 College Street N.W., Washington, DC 20059, USA
*Correspondence e-mail: jsmatthews@howard.edu

(Received 22 October 2011; accepted 27 October 2011; online 5 November 2011)

The title compound, [Zn(C8H14NO2)2], represents a zinc complex with the Zn2+ cation coordinated by two O and two N atoms in a distorted tetrahedral geometry.

Related literature

For background to ZnO and its applications, see: Norton et al. (2004[Norton, D. P., Heo, Y. W., Ivill, M. P., Ip, K., Pearton, S. J., Chisholm, M. F. & Steiner, T. (2004). Mater. Today, 7, 34-40.]); Groenen et al. (2005[Groenen, R., Loeffler, J., Linden, J. L., Schropp, R. E. I. & Van de Sanden, M. C. M. (2005). Thin Solid Films, 492, 298-306.]); Wan et al. (2004[Wan, Q., Li, Q., Chen, Y., Wang, T., He, X., Li, J. & Lin, C. (2004). Appl. Phys. Lett. 84, 3654-3656.]). For the growth of ZnO, see: Tribolate et al. (1999[Tribolate, R., N'tep, J. M., Barbe, M., Lemasson, P., Mora-Sero, I. & Munoz, V. J. (1999). J. Cryst. Growth, 198/199, 968-974.]); Fan et al. (2005[Fan, X. M., Lian, J. S., Guo, Z. X. & Lu, H. (2005). Appl. Surf. Sci. 239, 176-181.]); El Hichou et al. (2004[El Hichou, A., Addou, M., Bougrine, A., Dounia, R., Ebothe, J., Troyon, M. & Amrani, M. (2004). Mater. Chem. Phys. 83, 43-47.]); Hoon et al. (2011[Hoon, W. J., Chan, Y. K., Krishnasamy, J., Tou, Y. T. & Knipp, D. (2011). Appl. Surf. Sci. 257, 2508-2515.]); Jong et al. (2009[Jong, P. P., Sin, K. K., Park, J. Y., Ok, K. M. & Shim, W. (2009). Bull. Korean Chem. Soc. 30, 114-118.]); Malandrino et al. (2005[Malandrino, G., Balandino, M., Laura, M., Perdicaro, S. & Fragala, I. L. (2005). Inorg. Chem. 44, 9684-9689.]). For ZnO precursors, see: Smith (1983[Smith, F. (1983). Appl. Phys. Lett. 43, 1108-1110.]); Sato et al. (1994[Sato, H., Minami, T., Miyata, T., Takata, S. & Ishii, M. (1994). Thin Solid Films, 246, 65-70.]). The corresponding complex is a monomer; its structure consists of a Zn2+ cation with a distorted tetrahedral coordin­ation (Matthews et al., 2006[Matthews, J. S., Onakoya, O. O., Ouattara, T. S. & Butcher, R. J. (2006). Dalton Trans. pp. 3806-3811.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C8H14NO2)2]

  • Mr = 377.77

  • Triclinic, [P \overline 1]

  • a = 7.8087 (5) Å

  • b = 9.4353 (6) Å

  • c = 12.8788 (11) Å

  • α = 76.820 (3)°

  • β = 77.381 (3)°

  • γ = 83.413 (3)°

  • V = 899.46 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.39 mm−1

  • T = 103 K

  • 0.64 × 0.51 × 0.13 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.471, Tmax = 0.840

  • 9957 measured reflections

  • 4977 independent reflections

  • 4508 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 0.070

  • S = 1.00

  • 4977 reflections

  • 214 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Selected geometric parameters (Å, °)

Zn—O1B 1.9784 (10)
Zn—N1A 1.9784 (12)
Zn—N1B 1.9785 (11)
Zn—O1A 1.9963 (10)
O1B—Zn—N1A 117.85 (4)
O1B—Zn—N1B 97.63 (4)
N1A—Zn—N1B 123.66 (5)
O1B—Zn—O1A 106.41 (4)
N1A—Zn—O1A 96.73 (5)
N1B—Zn—O1A 114.34 (5)

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Novel precursors have been synthesized and utilized in the growth of ZnO thin films via metal-organic chemical vapor deposition (MOCVD). ZnO is a wide band gap (3.37ev) semiconductor, with several favorable properties including good transparency, high electron mobility, strong room-temperature luminescence and piezoelectric properties (Norton et al., 2004). ZnO has a variety of potential applications such as gas sensors, ultraviolet light-emitting diodes, solar cells, photodetectors, transistors and laser systems (Groenen et al., 2005) and (Wan et al., 2004). These applications of ZnO have propelled researchers to develop methods for the growth of ZnO thin films. Techniques that have been employed include sublimation (Tribolate et al., 1999), pulsed-laser deposition (PLD) (Fan et al., 2005), spray pyrolysis (SP) (El Hichou et al., 2004), magnetron sputtering (Hoon et al., 2011) and MOCVD (Jong et al., 2009). MOCVD has proven to be a promising method for ZnO growth due to a high degree of controllability of the film composition, capability for large scale area growth, high growth rate, prefered orientation and high quality thin films (Malandrino et al., 2005). In order for the MOCVD process to produce uniform and reproducible films, the precursors employed need to be volatile and thermally stable. Previous studies have reported the use of metal alkyls such as diethyzinc in combination with an oxygen source (e.g.H2O or ROH) (Smith, 1983). The drawback with these precursors is that gas-phase pre-reaction occurs resulting in film contamination and precursor decomposition. In addition, dialkyzinc precursors of acetate, alkoxide and acetylacetonate have been employed (Sato et al., 1994), however impurities are often found in prepared ZnO films. These drawbacks have sparked researchers interest in developing more favorable precursors for growing ZnO. Our research group has investigated the use of β-ketoiminate and β-iminoesterate ligand platforms for growing ZnO thin films (Matthews et al., 2006). Herein we describe the synthesis, characterization, of a novel bis β-iminoesterate.The bond lengths and angles of the reported compound were compared to an analogous Zn bis β-iminoesterate complex that has been previously reported (Matthews et al., 2006). The Zn—O bond lengths for the reported compound are longer than that observed for the analogous complex whose bond lengths measure 1.9454 Å and 1.9572 Å respectively. The Zn—N bond lengths are also longer in the analogous compound measuring 1.9475 Å and 1.9491 Å respectively. The is no difference between the Zn—O(1B) and Zn—N(1 A) bond lengths of 1.974 Å. However, Zn—O(1 A) and Zn—N(1B) measure 1.9963 Å and 1.9785 Å respectively.

Related literature top

For background to ZnO and its applications, see: Norton et al. (2004); Groenen et al. (2005); Wan et al. (2004). For the growth of ZnO, see: Tribolate et al. (1999); Fan et al. (2005); El Hichou et al. (2004); Hoon et al. (2011); Jong et al. (2009); Malandrino et al. (2005). For ZnO precursors, see: Smith (1983); Sato et al. (1994). The corresponding four-coordinate complex is a monomer and it consists of a distorted tetrahedral Zn atom (Matthews et al., 2006).

Experimental top

Synthesis of bis [Methyl 3-N-(propylimino)butanoato] zinc (II) To a 100 ml round bottom flask Under an inert atmosphere of dry nitrogen, 2.00 g (12.7 mmol) of Methyl 3-N-(propylimino)butanoate was added to a Schlenk flask containing 50 ml of dried hexanes and a magnetic stir bar. The mixture was cooled to 0° and 6.4 ml s of diethyl zinc (1.0 M) was added drop wise by syringe. The mixture was allowed to warm up to room temperature and stirred for 1 h. The solvent was removed in vaccuo to afford a white solid. The isolated solid was dissolved in dry pentane and held at -5 °C for 2 days at which time the formation of colorless crystals was observed. Spectroscopic Analysis: 1H NMR 400 MHz, CDCl3, δ p.p.m.: 0.83 (t, 6H, CH3CH2CH2), 1.42 (m, 4H, CH3CH2CH2), 1.90 (s, 6H, CH3CN), 3.12 (m, 2H, CH3CH2CH), 3.20 (m, 2H, CH3CH2CH), 3.57 (s, 6H, OCH3), 4.28 (s, 2H, CCHCO); 13C NMR 100 MHz, CDCl3, δ p.p.m.: 11.70 [CH3CH2CH2], 22.19 [CH3CH2CH2], 24.63 [CH3CN], 50.89 [CH3CH2CH2], 52.30 [OCH3], 77.31 [CHCO], 171.54 [CH3CN], 172.31 [CHCO].

Refinement top

H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 and 0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Structure description top

Novel precursors have been synthesized and utilized in the growth of ZnO thin films via metal-organic chemical vapor deposition (MOCVD). ZnO is a wide band gap (3.37ev) semiconductor, with several favorable properties including good transparency, high electron mobility, strong room-temperature luminescence and piezoelectric properties (Norton et al., 2004). ZnO has a variety of potential applications such as gas sensors, ultraviolet light-emitting diodes, solar cells, photodetectors, transistors and laser systems (Groenen et al., 2005) and (Wan et al., 2004). These applications of ZnO have propelled researchers to develop methods for the growth of ZnO thin films. Techniques that have been employed include sublimation (Tribolate et al., 1999), pulsed-laser deposition (PLD) (Fan et al., 2005), spray pyrolysis (SP) (El Hichou et al., 2004), magnetron sputtering (Hoon et al., 2011) and MOCVD (Jong et al., 2009). MOCVD has proven to be a promising method for ZnO growth due to a high degree of controllability of the film composition, capability for large scale area growth, high growth rate, prefered orientation and high quality thin films (Malandrino et al., 2005). In order for the MOCVD process to produce uniform and reproducible films, the precursors employed need to be volatile and thermally stable. Previous studies have reported the use of metal alkyls such as diethyzinc in combination with an oxygen source (e.g.H2O or ROH) (Smith, 1983). The drawback with these precursors is that gas-phase pre-reaction occurs resulting in film contamination and precursor decomposition. In addition, dialkyzinc precursors of acetate, alkoxide and acetylacetonate have been employed (Sato et al., 1994), however impurities are often found in prepared ZnO films. These drawbacks have sparked researchers interest in developing more favorable precursors for growing ZnO. Our research group has investigated the use of β-ketoiminate and β-iminoesterate ligand platforms for growing ZnO thin films (Matthews et al., 2006). Herein we describe the synthesis, characterization, of a novel bis β-iminoesterate.The bond lengths and angles of the reported compound were compared to an analogous Zn bis β-iminoesterate complex that has been previously reported (Matthews et al., 2006). The Zn—O bond lengths for the reported compound are longer than that observed for the analogous complex whose bond lengths measure 1.9454 Å and 1.9572 Å respectively. The Zn—N bond lengths are also longer in the analogous compound measuring 1.9475 Å and 1.9491 Å respectively. The is no difference between the Zn—O(1B) and Zn—N(1 A) bond lengths of 1.974 Å. However, Zn—O(1 A) and Zn—N(1B) measure 1.9963 Å and 1.9785 Å respectively.

For background to ZnO and its applications, see: Norton et al. (2004); Groenen et al. (2005); Wan et al. (2004). For the growth of ZnO, see: Tribolate et al. (1999); Fan et al. (2005); El Hichou et al. (2004); Hoon et al. (2011); Jong et al. (2009); Malandrino et al. (2005). For ZnO precursors, see: Smith (1983); Sato et al. (1994). The corresponding four-coordinate complex is a monomer and it consists of a distorted tetrahedral Zn atom (Matthews et al., 2006).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 20% probability level and H atoms are shown as spheres of arbitrary radius.
Bis[methyl 3-(propylamino)but-2-enoato]zinc top
Crystal data top
[Zn(C8H14NO2)2]Z = 2
Mr = 377.77F(000) = 400
Triclinic, P1Dx = 1.395 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8087 (5) ÅCell parameters from 7001 reflections
b = 9.4353 (6) Åθ = 2.3–24.6°
c = 12.8788 (11) ŵ = 1.39 mm1
α = 76.820 (3)°T = 103 K
β = 77.381 (3)°Plate, colourless
γ = 83.413 (3)°0.64 × 0.51 × 0.13 mm
V = 899.46 (11) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4977 independent reflections
Radiation source: fine-focus sealed tube4508 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
phi and ω scansθmax = 30.7°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 911
Tmin = 0.471, Tmax = 0.840k = 1212
9957 measured reflectionsl = 1718
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0336P)2 + 0.4769P]
where P = (Fo2 + 2Fc2)/3
4977 reflections(Δ/σ)max = 0.003
214 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
[Zn(C8H14NO2)2]γ = 83.413 (3)°
Mr = 377.77V = 899.46 (11) Å3
Triclinic, P1Z = 2
a = 7.8087 (5) ÅMo Kα radiation
b = 9.4353 (6) ŵ = 1.39 mm1
c = 12.8788 (11) ÅT = 103 K
α = 76.820 (3)°0.64 × 0.51 × 0.13 mm
β = 77.381 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4977 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
4508 reflections with I > 2σ(I)
Tmin = 0.471, Tmax = 0.840Rint = 0.020
9957 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.070H-atom parameters constrained
S = 1.00Δρmax = 0.82 e Å3
4977 reflectionsΔρmin = 0.54 e Å3
214 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
Zn0.54308 (2)0.924864 (17)0.751108 (12)0.01951 (5)
O1A0.32476 (13)0.81656 (11)0.79509 (8)0.0236 (2)
O2A0.15956 (15)0.64045 (12)0.90620 (9)0.0302 (2)
O1B0.46956 (13)1.13117 (11)0.69599 (8)0.02141 (19)
O2B0.47457 (14)1.33455 (11)0.56379 (8)0.0244 (2)
N1A0.61225 (15)0.87359 (13)0.89469 (9)0.0202 (2)
N1B0.69909 (15)0.88855 (13)0.61512 (9)0.0199 (2)
C1A0.0663 (2)0.65066 (19)0.82025 (14)0.0326 (3)
H1AA0.02580.58130.84390.049*
H1AB0.14830.62780.75600.049*
H1AC0.01270.74990.80210.049*
C2A0.30075 (18)0.72305 (15)0.88369 (11)0.0225 (3)
C3A0.3992 (2)0.69008 (16)0.96517 (11)0.0246 (3)
H3AA0.36580.60991.02330.030*
C4A0.54370 (19)0.76365 (15)0.97014 (11)0.0212 (3)
C5A0.6216 (2)0.70783 (17)1.07104 (12)0.0276 (3)
H5AA0.74700.67991.04960.041*
H5AB0.56090.62271.11600.041*
H5AC0.60730.78481.11270.041*
C6A0.75495 (18)0.94490 (15)0.91732 (11)0.0217 (3)
H6AA0.85260.87120.93170.026*
H6AB0.71050.98520.98350.026*
C7A0.8239 (2)1.06658 (16)0.82344 (12)0.0252 (3)
H7AA0.72861.14370.81200.030*
H7AB0.86211.02790.75610.030*
C8A0.9787 (2)1.13208 (18)0.84601 (13)0.0303 (3)
H8AA1.01791.21300.78560.045*
H8AB1.07561.05710.85330.045*
H8AC0.94171.16820.91360.045*
C1B0.3431 (2)1.40060 (16)0.63758 (12)0.0254 (3)
H1BA0.31521.50190.60300.038*
H1BB0.38711.39860.70360.038*
H1BC0.23671.34660.65670.038*
C2B0.53266 (17)1.19383 (15)0.59936 (11)0.0198 (2)
C3B0.65608 (19)1.13903 (16)0.52004 (11)0.0227 (3)
H3BA0.69491.20610.45390.027*
C4B0.72970 (17)0.99394 (15)0.52762 (11)0.0203 (2)
C5B0.8511 (2)0.96427 (17)0.42470 (11)0.0251 (3)
H5BA0.96070.91280.44250.038*
H5BB0.87731.05690.37350.038*
H5BC0.79380.90390.39150.038*
C6B0.78253 (19)0.74229 (15)0.60851 (12)0.0239 (3)
H6BA0.90670.73920.61560.029*
H6BB0.78190.72330.53610.029*
C7B0.6909 (2)0.62329 (16)0.69560 (13)0.0276 (3)
H7BA0.56600.62700.68990.033*
H7BB0.69460.63970.76830.033*
C8B0.7791 (2)0.47334 (17)0.68364 (15)0.0345 (3)
H8BA0.72010.39830.74210.052*
H8BB0.90320.47020.68810.052*
H8BC0.77060.45520.61300.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.01943 (8)0.02190 (8)0.01611 (8)0.00083 (6)0.00332 (5)0.00224 (5)
O1A0.0198 (5)0.0271 (5)0.0231 (5)0.0020 (4)0.0047 (4)0.0026 (4)
O2A0.0254 (5)0.0325 (6)0.0328 (6)0.0100 (4)0.0064 (4)0.0023 (4)
O1B0.0212 (5)0.0235 (5)0.0181 (4)0.0015 (4)0.0029 (4)0.0023 (4)
O2B0.0245 (5)0.0230 (5)0.0217 (5)0.0005 (4)0.0015 (4)0.0003 (4)
N1A0.0203 (5)0.0225 (5)0.0181 (5)0.0012 (4)0.0037 (4)0.0048 (4)
N1B0.0175 (5)0.0237 (5)0.0195 (5)0.0019 (4)0.0048 (4)0.0055 (4)
C1A0.0245 (7)0.0379 (8)0.0389 (8)0.0046 (6)0.0085 (6)0.0120 (7)
C2A0.0197 (6)0.0222 (6)0.0244 (6)0.0017 (5)0.0011 (5)0.0054 (5)
C3A0.0273 (7)0.0235 (6)0.0212 (6)0.0043 (5)0.0034 (5)0.0013 (5)
C4A0.0224 (6)0.0223 (6)0.0181 (6)0.0019 (5)0.0033 (5)0.0048 (5)
C5A0.0337 (8)0.0294 (7)0.0189 (6)0.0040 (6)0.0074 (5)0.0003 (5)
C6A0.0203 (6)0.0258 (6)0.0196 (6)0.0016 (5)0.0046 (5)0.0055 (5)
C7A0.0219 (7)0.0296 (7)0.0233 (6)0.0043 (5)0.0044 (5)0.0028 (5)
C8A0.0225 (7)0.0362 (8)0.0323 (7)0.0074 (6)0.0047 (6)0.0054 (6)
C1B0.0256 (7)0.0230 (6)0.0244 (6)0.0011 (5)0.0022 (5)0.0026 (5)
C2B0.0163 (6)0.0224 (6)0.0209 (6)0.0030 (5)0.0062 (5)0.0019 (5)
C3B0.0205 (6)0.0254 (6)0.0196 (6)0.0036 (5)0.0019 (5)0.0005 (5)
C4B0.0152 (6)0.0285 (6)0.0188 (6)0.0034 (5)0.0047 (4)0.0062 (5)
C5B0.0227 (7)0.0326 (7)0.0196 (6)0.0028 (5)0.0016 (5)0.0065 (5)
C6B0.0235 (7)0.0249 (6)0.0237 (6)0.0002 (5)0.0038 (5)0.0076 (5)
C7B0.0242 (7)0.0234 (7)0.0331 (7)0.0011 (5)0.0028 (6)0.0048 (6)
C8B0.0321 (8)0.0245 (7)0.0447 (9)0.0001 (6)0.0043 (7)0.0070 (6)
Geometric parameters (Å, º) top
Zn—O1B1.9784 (10)C6A—H6AB0.9900
Zn—N1A1.9784 (12)C7A—C8A1.527 (2)
Zn—N1B1.9785 (11)C7A—H7AA0.9900
Zn—O1A1.9963 (10)C7A—H7AB0.9900
O1A—C2A1.2653 (17)C8A—H8AA0.9800
O2A—C2A1.3644 (17)C8A—H8AB0.9800
O2A—C1A1.432 (2)C8A—H8AC0.9800
O1B—C2B1.2666 (16)C1B—H1BA0.9800
O2B—C2B1.3615 (16)C1B—H1BB0.9800
O2B—C1B1.4292 (17)C1B—H1BC0.9800
N1A—C4A1.3218 (18)C2B—C3B1.3915 (19)
N1A—C6A1.4773 (18)C3B—C4B1.413 (2)
N1B—C4B1.3197 (18)C3B—H3BA0.9500
N1B—C6B1.4694 (18)C4B—C5B1.5143 (19)
C1A—H1AA0.9800C5B—H5BA0.9800
C1A—H1AB0.9800C5B—H5BB0.9800
C1A—H1AC0.9800C5B—H5BC0.9800
C2A—C3A1.392 (2)C6B—C7B1.513 (2)
C3A—C4A1.411 (2)C6B—H6BA0.9900
C3A—H3AA0.9500C6B—H6BB0.9900
C4A—C5A1.515 (2)C7B—C8B1.526 (2)
C5A—H5AA0.9800C7B—H7BA0.9900
C5A—H5AB0.9800C7B—H7BB0.9900
C5A—H5AC0.9800C8B—H8BA0.9800
C6A—C7A1.515 (2)C8B—H8BB0.9800
C6A—H6AA0.9900C8B—H8BC0.9800
O1B—Zn—N1A117.85 (4)C8A—C7A—H7AB109.5
O1B—Zn—N1B97.63 (4)H7AA—C7A—H7AB108.0
N1A—Zn—N1B123.66 (5)C7A—C8A—H8AA109.5
O1B—Zn—O1A106.41 (4)C7A—C8A—H8AB109.5
N1A—Zn—O1A96.73 (5)H8AA—C8A—H8AB109.5
N1B—Zn—O1A114.34 (5)C7A—C8A—H8AC109.5
C2A—O1A—Zn119.24 (9)H8AA—C8A—H8AC109.5
C2A—O2A—C1A116.87 (12)H8AB—C8A—H8AC109.5
C2B—O1B—Zn120.03 (9)O2B—C1B—H1BA109.5
C2B—O2B—C1B117.56 (11)O2B—C1B—H1BB109.5
C4A—N1A—C6A117.53 (12)H1BA—C1B—H1BB109.5
C4A—N1A—Zn120.54 (10)O2B—C1B—H1BC109.5
C6A—N1A—Zn121.60 (9)H1BA—C1B—H1BC109.5
C4B—N1B—C6B118.11 (11)H1BB—C1B—H1BC109.5
C4B—N1B—Zn121.21 (9)O1B—C2B—O2B118.07 (12)
C6B—N1B—Zn120.67 (9)O1B—C2B—C3B129.19 (13)
O2A—C1A—H1AA109.5O2B—C2B—C3B112.75 (12)
O2A—C1A—H1AB109.5C2B—C3B—C4B126.74 (13)
H1AA—C1A—H1AB109.5C2B—C3B—H3BA116.6
O2A—C1A—H1AC109.5C4B—C3B—H3BA116.6
H1AA—C1A—H1AC109.5N1B—C4B—C3B124.95 (12)
H1AB—C1A—H1AC109.5N1B—C4B—C5B120.39 (12)
O1A—C2A—O2A117.82 (13)C3B—C4B—C5B114.65 (12)
O1A—C2A—C3A129.20 (13)C4B—C5B—H5BA109.5
O2A—C2A—C3A112.99 (12)C4B—C5B—H5BB109.5
C2A—C3A—C4A126.59 (13)H5BA—C5B—H5BB109.5
C2A—C3A—H3AA116.7C4B—C5B—H5BC109.5
C4A—C3A—H3AA116.7H5BA—C5B—H5BC109.5
N1A—C4A—C3A124.94 (13)H5BB—C5B—H5BC109.5
N1A—C4A—C5A119.84 (13)N1B—C6B—C7B112.72 (11)
C3A—C4A—C5A115.22 (12)N1B—C6B—H6BA109.0
C4A—C5A—H5AA109.5C7B—C6B—H6BA109.0
C4A—C5A—H5AB109.5N1B—C6B—H6BB109.0
H5AA—C5A—H5AB109.5C7B—C6B—H6BB109.0
C4A—C5A—H5AC109.5H6BA—C6B—H6BB107.8
H5AA—C5A—H5AC109.5C6B—C7B—C8B110.83 (13)
H5AB—C5A—H5AC109.5C6B—C7B—H7BA109.5
N1A—C6A—C7A112.03 (11)C8B—C7B—H7BA109.5
N1A—C6A—H6AA109.2C6B—C7B—H7BB109.5
C7A—C6A—H6AA109.2C8B—C7B—H7BB109.5
N1A—C6A—H6AB109.2H7BA—C7B—H7BB108.1
C7A—C6A—H6AB109.2C7B—C8B—H8BA109.5
H6AA—C6A—H6AB107.9C7B—C8B—H8BB109.5
C6A—C7A—C8A110.95 (12)H8BA—C8B—H8BB109.5
C6A—C7A—H7AA109.5C7B—C8B—H8BC109.5
C8A—C7A—H7AA109.5H8BA—C8B—H8BC109.5
C6A—C7A—H7AB109.5H8BB—C8B—H8BC109.5
O1B—Zn—O1A—C2A136.62 (10)C6A—N1A—C4A—C3A175.45 (13)
N1A—Zn—O1A—C2A14.94 (11)Zn—N1A—C4A—C3A11.12 (19)
N1B—Zn—O1A—C2A116.82 (10)C6A—N1A—C4A—C5A4.78 (18)
N1A—Zn—O1B—C2B132.15 (10)Zn—N1A—C4A—C5A168.66 (10)
N1B—Zn—O1B—C2B2.54 (11)C2A—C3A—C4A—N1A2.6 (2)
O1A—Zn—O1B—C2B120.76 (10)C2A—C3A—C4A—C5A177.56 (14)
O1B—Zn—N1A—C4A129.69 (10)C4A—N1A—C6A—C7A178.77 (12)
N1B—Zn—N1A—C4A108.15 (11)Zn—N1A—C6A—C7A5.41 (15)
O1A—Zn—N1A—C4A17.10 (11)N1A—C6A—C7A—C8A176.50 (12)
O1B—Zn—N1A—C6A57.14 (11)Zn—O1B—C2B—O2B178.12 (9)
N1B—Zn—N1A—C6A65.01 (11)Zn—O1B—C2B—C3B1.2 (2)
O1A—Zn—N1A—C6A169.74 (10)C1B—O2B—C2B—O1B1.40 (18)
O1B—Zn—N1B—C4B3.50 (11)C1B—O2B—C2B—C3B178.06 (12)
N1A—Zn—N1B—C4B127.45 (10)O1B—C2B—C3B—C4B5.5 (3)
O1A—Zn—N1B—C4B115.43 (10)O2B—C2B—C3B—C4B173.93 (13)
O1B—Zn—N1B—C6B175.72 (10)C6B—N1B—C4B—C3B178.33 (13)
N1A—Zn—N1B—C6B53.32 (12)Zn—N1B—C4B—C3B0.91 (19)
O1A—Zn—N1B—C6B63.79 (11)C6B—N1B—C4B—C5B1.41 (19)
Zn—O1A—C2A—O2A173.49 (9)Zn—N1B—C4B—C5B179.35 (10)
Zn—O1A—C2A—C3A6.7 (2)C2B—C3B—C4B—N1B4.1 (2)
C1A—O2A—C2A—O1A9.44 (19)C2B—C3B—C4B—C5B175.68 (14)
C1A—O2A—C2A—C3A170.72 (13)C4B—N1B—C6B—C7B159.60 (13)
O1A—C2A—C3A—C4A5.2 (3)Zn—N1B—C6B—C7B19.65 (16)
O2A—C2A—C3A—C4A174.58 (13)N1B—C6B—C7B—C8B178.50 (13)

Experimental details

Crystal data
Chemical formula[Zn(C8H14NO2)2]
Mr377.77
Crystal system, space groupTriclinic, P1
Temperature (K)103
a, b, c (Å)7.8087 (5), 9.4353 (6), 12.8788 (11)
α, β, γ (°)76.820 (3), 77.381 (3), 83.413 (3)
V3)899.46 (11)
Z2
Radiation typeMo Kα
µ (mm1)1.39
Crystal size (mm)0.64 × 0.51 × 0.13
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.471, 0.840
No. of measured, independent and
observed [I > 2σ(I)] reflections
9957, 4977, 4508
Rint0.020
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.070, 1.00
No. of reflections4977
No. of parameters214
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 0.54

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Zn—O1B1.9784 (10)Zn—N1B1.9785 (11)
Zn—N1A1.9784 (12)Zn—O1A1.9963 (10)
O1B—Zn—N1A117.85 (4)O1B—Zn—O1A106.41 (4)
O1B—Zn—N1B97.63 (4)N1A—Zn—O1A96.73 (5)
N1A—Zn—N1B123.66 (5)N1B—Zn—O1A114.34 (5)
 

Acknowledgements

The authors thank NSF-PREM #0611595 for financial support.

References

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