Abstract
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 ▶); 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 complex is a monomer; its structure consists of a Zn2+ cation with a distorted tetrahedral coordination (Matthews et al., 2006 ▶).
Experimental
Crystal data
[Zn(C8H14NO2)2]
M r = 377.77
Triclinic,
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 ▶) T min = 0.471, T max = 0.840
9957 measured reflections
4977 independent reflections
4508 reflections with I > 2σ(I)
R int = 0.020
Refinement
R[F 2 > 2σ(F 2)] = 0.027
wR(F 2) = 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
Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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.
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104520X/bt5685sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104520X/bt5685Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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) |
Acknowledgments
The authors thank NSF-PREM #0611595 for financial support.
supplementary crystallographic information
Comment
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.
Experimental
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
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).
Figures
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.
Crystal data
| [Zn(C8H14NO2)2] | Z = 2 |
| Mr = 377.77 | F(000) = 400 |
| Triclinic, P1 | Dx = 1.395 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.8087 (5) Å | Cell parameters from 7001 reflections |
| b = 9.4353 (6) Å | θ = 2.3–24.6° |
| c = 12.8788 (11) Å | µ = 1.39 mm−1 |
| 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
| Bruker SMART CCD area-detector diffractometer | 4977 independent reflections |
| Radiation source: fine-focus sealed tube | 4508 reflections with I > 2σ(I) |
| graphite | Rint = 0.020 |
| phi and ω scans | θmax = 30.7°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −9→11 |
| Tmin = 0.471, Tmax = 0.840 | k = −12→12 |
| 9957 measured reflections | l = −17→18 |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.070 | H-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 parameters | Δρmax = 0.82 e Å−3 |
| 0 restraints | Δρmin = −0.54 e Å−3 |
Special details
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn | 0.54308 (2) | 0.924864 (17) | 0.751108 (12) | 0.01951 (5) | |
| O1A | 0.32476 (13) | 0.81656 (11) | 0.79509 (8) | 0.0236 (2) | |
| O2A | 0.15956 (15) | 0.64045 (12) | 0.90620 (9) | 0.0302 (2) | |
| O1B | 0.46956 (13) | 1.13117 (11) | 0.69599 (8) | 0.02141 (19) | |
| O2B | 0.47457 (14) | 1.33455 (11) | 0.56379 (8) | 0.0244 (2) | |
| N1A | 0.61225 (15) | 0.87359 (13) | 0.89469 (9) | 0.0202 (2) | |
| N1B | 0.69909 (15) | 0.88855 (13) | 0.61512 (9) | 0.0199 (2) | |
| C1A | 0.0663 (2) | 0.65066 (19) | 0.82025 (14) | 0.0326 (3) | |
| H1AA | −0.0258 | 0.5813 | 0.8439 | 0.049* | |
| H1AB | 0.1483 | 0.6278 | 0.7560 | 0.049* | |
| H1AC | 0.0127 | 0.7499 | 0.8021 | 0.049* | |
| C2A | 0.30075 (18) | 0.72305 (15) | 0.88369 (11) | 0.0225 (3) | |
| C3A | 0.3992 (2) | 0.69008 (16) | 0.96517 (11) | 0.0246 (3) | |
| H3AA | 0.3658 | 0.6099 | 1.0233 | 0.030* | |
| C4A | 0.54370 (19) | 0.76365 (15) | 0.97014 (11) | 0.0212 (3) | |
| C5A | 0.6216 (2) | 0.70783 (17) | 1.07104 (12) | 0.0276 (3) | |
| H5AA | 0.7470 | 0.6799 | 1.0496 | 0.041* | |
| H5AB | 0.5609 | 0.6227 | 1.1160 | 0.041* | |
| H5AC | 0.6073 | 0.7848 | 1.1127 | 0.041* | |
| C6A | 0.75495 (18) | 0.94490 (15) | 0.91732 (11) | 0.0217 (3) | |
| H6AA | 0.8526 | 0.8712 | 0.9317 | 0.026* | |
| H6AB | 0.7105 | 0.9852 | 0.9835 | 0.026* | |
| C7A | 0.8239 (2) | 1.06658 (16) | 0.82344 (12) | 0.0252 (3) | |
| H7AA | 0.7286 | 1.1437 | 0.8120 | 0.030* | |
| H7AB | 0.8621 | 1.0279 | 0.7561 | 0.030* | |
| C8A | 0.9787 (2) | 1.13208 (18) | 0.84601 (13) | 0.0303 (3) | |
| H8AA | 1.0179 | 1.2130 | 0.7856 | 0.045* | |
| H8AB | 1.0756 | 1.0571 | 0.8533 | 0.045* | |
| H8AC | 0.9417 | 1.1682 | 0.9136 | 0.045* | |
| C1B | 0.3431 (2) | 1.40060 (16) | 0.63758 (12) | 0.0254 (3) | |
| H1BA | 0.3152 | 1.5019 | 0.6030 | 0.038* | |
| H1BB | 0.3871 | 1.3986 | 0.7036 | 0.038* | |
| H1BC | 0.2367 | 1.3466 | 0.6567 | 0.038* | |
| C2B | 0.53266 (17) | 1.19383 (15) | 0.59936 (11) | 0.0198 (2) | |
| C3B | 0.65608 (19) | 1.13903 (16) | 0.52004 (11) | 0.0227 (3) | |
| H3BA | 0.6949 | 1.2061 | 0.4539 | 0.027* | |
| C4B | 0.72970 (17) | 0.99394 (15) | 0.52762 (11) | 0.0203 (2) | |
| C5B | 0.8511 (2) | 0.96427 (17) | 0.42470 (11) | 0.0251 (3) | |
| H5BA | 0.9607 | 0.9128 | 0.4425 | 0.038* | |
| H5BB | 0.8773 | 1.0569 | 0.3735 | 0.038* | |
| H5BC | 0.7938 | 0.9039 | 0.3915 | 0.038* | |
| C6B | 0.78253 (19) | 0.74229 (15) | 0.60851 (12) | 0.0239 (3) | |
| H6BA | 0.9067 | 0.7392 | 0.6156 | 0.029* | |
| H6BB | 0.7819 | 0.7233 | 0.5361 | 0.029* | |
| C7B | 0.6909 (2) | 0.62329 (16) | 0.69560 (13) | 0.0276 (3) | |
| H7BA | 0.5660 | 0.6270 | 0.6899 | 0.033* | |
| H7BB | 0.6946 | 0.6397 | 0.7683 | 0.033* | |
| C8B | 0.7791 (2) | 0.47334 (17) | 0.68364 (15) | 0.0345 (3) | |
| H8BA | 0.7201 | 0.3983 | 0.7421 | 0.052* | |
| H8BB | 0.9032 | 0.4702 | 0.6881 | 0.052* | |
| H8BC | 0.7706 | 0.4552 | 0.6130 | 0.052* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn | 0.01943 (8) | 0.02190 (8) | 0.01611 (8) | −0.00083 (6) | −0.00332 (5) | −0.00224 (5) |
| O1A | 0.0198 (5) | 0.0271 (5) | 0.0231 (5) | −0.0020 (4) | −0.0047 (4) | −0.0026 (4) |
| O2A | 0.0254 (5) | 0.0325 (6) | 0.0328 (6) | −0.0100 (4) | −0.0064 (4) | −0.0023 (4) |
| O1B | 0.0212 (5) | 0.0235 (5) | 0.0181 (4) | −0.0015 (4) | −0.0029 (4) | −0.0023 (4) |
| O2B | 0.0245 (5) | 0.0230 (5) | 0.0217 (5) | 0.0005 (4) | −0.0015 (4) | −0.0003 (4) |
| N1A | 0.0203 (5) | 0.0225 (5) | 0.0181 (5) | −0.0012 (4) | −0.0037 (4) | −0.0048 (4) |
| N1B | 0.0175 (5) | 0.0237 (5) | 0.0195 (5) | −0.0019 (4) | −0.0048 (4) | −0.0055 (4) |
| C1A | 0.0245 (7) | 0.0379 (8) | 0.0389 (8) | −0.0046 (6) | −0.0085 (6) | −0.0120 (7) |
| C2A | 0.0197 (6) | 0.0222 (6) | 0.0244 (6) | −0.0017 (5) | −0.0011 (5) | −0.0054 (5) |
| C3A | 0.0273 (7) | 0.0235 (6) | 0.0212 (6) | −0.0043 (5) | −0.0034 (5) | −0.0013 (5) |
| C4A | 0.0224 (6) | 0.0223 (6) | 0.0181 (6) | 0.0019 (5) | −0.0033 (5) | −0.0048 (5) |
| C5A | 0.0337 (8) | 0.0294 (7) | 0.0189 (6) | −0.0040 (6) | −0.0074 (5) | −0.0003 (5) |
| C6A | 0.0203 (6) | 0.0258 (6) | 0.0196 (6) | −0.0016 (5) | −0.0046 (5) | −0.0055 (5) |
| C7A | 0.0219 (7) | 0.0296 (7) | 0.0233 (6) | −0.0043 (5) | −0.0044 (5) | −0.0028 (5) |
| C8A | 0.0225 (7) | 0.0362 (8) | 0.0323 (7) | −0.0074 (6) | −0.0047 (6) | −0.0054 (6) |
| C1B | 0.0256 (7) | 0.0230 (6) | 0.0244 (6) | 0.0011 (5) | −0.0022 (5) | −0.0026 (5) |
| C2B | 0.0163 (6) | 0.0224 (6) | 0.0209 (6) | −0.0030 (5) | −0.0062 (5) | −0.0019 (5) |
| C3B | 0.0205 (6) | 0.0254 (6) | 0.0196 (6) | −0.0036 (5) | −0.0019 (5) | −0.0005 (5) |
| C4B | 0.0152 (6) | 0.0285 (6) | 0.0188 (6) | −0.0034 (5) | −0.0047 (4) | −0.0062 (5) |
| C5B | 0.0227 (7) | 0.0326 (7) | 0.0196 (6) | −0.0028 (5) | −0.0016 (5) | −0.0065 (5) |
| C6B | 0.0235 (7) | 0.0249 (6) | 0.0237 (6) | 0.0002 (5) | −0.0038 (5) | −0.0076 (5) |
| C7B | 0.0242 (7) | 0.0234 (7) | 0.0331 (7) | −0.0011 (5) | −0.0028 (6) | −0.0048 (6) |
| C8B | 0.0321 (8) | 0.0245 (7) | 0.0447 (9) | 0.0001 (6) | −0.0043 (7) | −0.0070 (6) |
Geometric parameters (Å, °)
| Zn—O1B | 1.9784 (10) | C6A—H6AB | 0.9900 |
| Zn—N1A | 1.9784 (12) | C7A—C8A | 1.527 (2) |
| Zn—N1B | 1.9785 (11) | C7A—H7AA | 0.9900 |
| Zn—O1A | 1.9963 (10) | C7A—H7AB | 0.9900 |
| O1A—C2A | 1.2653 (17) | C8A—H8AA | 0.9800 |
| O2A—C2A | 1.3644 (17) | C8A—H8AB | 0.9800 |
| O2A—C1A | 1.432 (2) | C8A—H8AC | 0.9800 |
| O1B—C2B | 1.2666 (16) | C1B—H1BA | 0.9800 |
| O2B—C2B | 1.3615 (16) | C1B—H1BB | 0.9800 |
| O2B—C1B | 1.4292 (17) | C1B—H1BC | 0.9800 |
| N1A—C4A | 1.3218 (18) | C2B—C3B | 1.3915 (19) |
| N1A—C6A | 1.4773 (18) | C3B—C4B | 1.413 (2) |
| N1B—C4B | 1.3197 (18) | C3B—H3BA | 0.9500 |
| N1B—C6B | 1.4694 (18) | C4B—C5B | 1.5143 (19) |
| C1A—H1AA | 0.9800 | C5B—H5BA | 0.9800 |
| C1A—H1AB | 0.9800 | C5B—H5BB | 0.9800 |
| C1A—H1AC | 0.9800 | C5B—H5BC | 0.9800 |
| C2A—C3A | 1.392 (2) | C6B—C7B | 1.513 (2) |
| C3A—C4A | 1.411 (2) | C6B—H6BA | 0.9900 |
| C3A—H3AA | 0.9500 | C6B—H6BB | 0.9900 |
| C4A—C5A | 1.515 (2) | C7B—C8B | 1.526 (2) |
| C5A—H5AA | 0.9800 | C7B—H7BA | 0.9900 |
| C5A—H5AB | 0.9800 | C7B—H7BB | 0.9900 |
| C5A—H5AC | 0.9800 | C8B—H8BA | 0.9800 |
| C6A—C7A | 1.515 (2) | C8B—H8BB | 0.9800 |
| C6A—H6AA | 0.9900 | C8B—H8BC | 0.9800 |
| O1B—Zn—N1A | 117.85 (4) | C8A—C7A—H7AB | 109.5 |
| O1B—Zn—N1B | 97.63 (4) | H7AA—C7A—H7AB | 108.0 |
| N1A—Zn—N1B | 123.66 (5) | C7A—C8A—H8AA | 109.5 |
| O1B—Zn—O1A | 106.41 (4) | C7A—C8A—H8AB | 109.5 |
| N1A—Zn—O1A | 96.73 (5) | H8AA—C8A—H8AB | 109.5 |
| N1B—Zn—O1A | 114.34 (5) | C7A—C8A—H8AC | 109.5 |
| C2A—O1A—Zn | 119.24 (9) | H8AA—C8A—H8AC | 109.5 |
| C2A—O2A—C1A | 116.87 (12) | H8AB—C8A—H8AC | 109.5 |
| C2B—O1B—Zn | 120.03 (9) | O2B—C1B—H1BA | 109.5 |
| C2B—O2B—C1B | 117.56 (11) | O2B—C1B—H1BB | 109.5 |
| C4A—N1A—C6A | 117.53 (12) | H1BA—C1B—H1BB | 109.5 |
| C4A—N1A—Zn | 120.54 (10) | O2B—C1B—H1BC | 109.5 |
| C6A—N1A—Zn | 121.60 (9) | H1BA—C1B—H1BC | 109.5 |
| C4B—N1B—C6B | 118.11 (11) | H1BB—C1B—H1BC | 109.5 |
| C4B—N1B—Zn | 121.21 (9) | O1B—C2B—O2B | 118.07 (12) |
| C6B—N1B—Zn | 120.67 (9) | O1B—C2B—C3B | 129.19 (13) |
| O2A—C1A—H1AA | 109.5 | O2B—C2B—C3B | 112.75 (12) |
| O2A—C1A—H1AB | 109.5 | C2B—C3B—C4B | 126.74 (13) |
| H1AA—C1A—H1AB | 109.5 | C2B—C3B—H3BA | 116.6 |
| O2A—C1A—H1AC | 109.5 | C4B—C3B—H3BA | 116.6 |
| H1AA—C1A—H1AC | 109.5 | N1B—C4B—C3B | 124.95 (12) |
| H1AB—C1A—H1AC | 109.5 | N1B—C4B—C5B | 120.39 (12) |
| O1A—C2A—O2A | 117.82 (13) | C3B—C4B—C5B | 114.65 (12) |
| O1A—C2A—C3A | 129.20 (13) | C4B—C5B—H5BA | 109.5 |
| O2A—C2A—C3A | 112.99 (12) | C4B—C5B—H5BB | 109.5 |
| C2A—C3A—C4A | 126.59 (13) | H5BA—C5B—H5BB | 109.5 |
| C2A—C3A—H3AA | 116.7 | C4B—C5B—H5BC | 109.5 |
| C4A—C3A—H3AA | 116.7 | H5BA—C5B—H5BC | 109.5 |
| N1A—C4A—C3A | 124.94 (13) | H5BB—C5B—H5BC | 109.5 |
| N1A—C4A—C5A | 119.84 (13) | N1B—C6B—C7B | 112.72 (11) |
| C3A—C4A—C5A | 115.22 (12) | N1B—C6B—H6BA | 109.0 |
| C4A—C5A—H5AA | 109.5 | C7B—C6B—H6BA | 109.0 |
| C4A—C5A—H5AB | 109.5 | N1B—C6B—H6BB | 109.0 |
| H5AA—C5A—H5AB | 109.5 | C7B—C6B—H6BB | 109.0 |
| C4A—C5A—H5AC | 109.5 | H6BA—C6B—H6BB | 107.8 |
| H5AA—C5A—H5AC | 109.5 | C6B—C7B—C8B | 110.83 (13) |
| H5AB—C5A—H5AC | 109.5 | C6B—C7B—H7BA | 109.5 |
| N1A—C6A—C7A | 112.03 (11) | C8B—C7B—H7BA | 109.5 |
| N1A—C6A—H6AA | 109.2 | C6B—C7B—H7BB | 109.5 |
| C7A—C6A—H6AA | 109.2 | C8B—C7B—H7BB | 109.5 |
| N1A—C6A—H6AB | 109.2 | H7BA—C7B—H7BB | 108.1 |
| C7A—C6A—H6AB | 109.2 | C7B—C8B—H8BA | 109.5 |
| H6AA—C6A—H6AB | 107.9 | C7B—C8B—H8BB | 109.5 |
| C6A—C7A—C8A | 110.95 (12) | H8BA—C8B—H8BB | 109.5 |
| C6A—C7A—H7AA | 109.5 | C7B—C8B—H8BC | 109.5 |
| C8A—C7A—H7AA | 109.5 | H8BA—C8B—H8BC | 109.5 |
| C6A—C7A—H7AB | 109.5 | H8BB—C8B—H8BC | 109.5 |
| O1B—Zn—O1A—C2A | −136.62 (10) | C6A—N1A—C4A—C3A | 175.45 (13) |
| N1A—Zn—O1A—C2A | −14.94 (11) | Zn—N1A—C4A—C3A | −11.12 (19) |
| N1B—Zn—O1A—C2A | 116.82 (10) | C6A—N1A—C4A—C5A | −4.78 (18) |
| N1A—Zn—O1B—C2B | 132.15 (10) | Zn—N1A—C4A—C5A | 168.66 (10) |
| N1B—Zn—O1B—C2B | −2.54 (11) | C2A—C3A—C4A—N1A | −2.6 (2) |
| O1A—Zn—O1B—C2B | −120.76 (10) | C2A—C3A—C4A—C5A | 177.56 (14) |
| O1B—Zn—N1A—C4A | 129.69 (10) | C4A—N1A—C6A—C7A | 178.77 (12) |
| N1B—Zn—N1A—C4A | −108.15 (11) | Zn—N1A—C6A—C7A | 5.41 (15) |
| O1A—Zn—N1A—C4A | 17.10 (11) | N1A—C6A—C7A—C8A | −176.50 (12) |
| O1B—Zn—N1A—C6A | −57.14 (11) | Zn—O1B—C2B—O2B | 178.12 (9) |
| N1B—Zn—N1A—C6A | 65.01 (11) | Zn—O1B—C2B—C3B | −1.2 (2) |
| O1A—Zn—N1A—C6A | −169.74 (10) | C1B—O2B—C2B—O1B | −1.40 (18) |
| O1B—Zn—N1B—C4B | 3.50 (11) | C1B—O2B—C2B—C3B | 178.06 (12) |
| N1A—Zn—N1B—C4B | −127.45 (10) | O1B—C2B—C3B—C4B | 5.5 (3) |
| O1A—Zn—N1B—C4B | 115.43 (10) | O2B—C2B—C3B—C4B | −173.93 (13) |
| O1B—Zn—N1B—C6B | −175.72 (10) | C6B—N1B—C4B—C3B | 178.33 (13) |
| N1A—Zn—N1B—C6B | 53.32 (12) | Zn—N1B—C4B—C3B | −0.91 (19) |
| O1A—Zn—N1B—C6B | −63.79 (11) | C6B—N1B—C4B—C5B | −1.41 (19) |
| Zn—O1A—C2A—O2A | −173.49 (9) | Zn—N1B—C4B—C5B | 179.35 (10) |
| Zn—O1A—C2A—C3A | 6.7 (2) | C2B—C3B—C4B—N1B | −4.1 (2) |
| C1A—O2A—C2A—O1A | 9.44 (19) | C2B—C3B—C4B—C5B | 175.68 (14) |
| C1A—O2A—C2A—C3A | −170.72 (13) | C4B—N1B—C6B—C7B | −159.60 (13) |
| O1A—C2A—C3A—C4A | 5.2 (3) | Zn—N1B—C6B—C7B | 19.65 (16) |
| O2A—C2A—C3A—C4A | −174.58 (13) | N1B—C6B—C7B—C8B | 178.50 (13) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5685).
References
- Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- El Hichou, A., Addou, M., Bougrine, A., Dounia, R., Ebothe, J., Troyon, M. & Amrani, M. (2004). Mater. Chem. Phys. 83, 43–47.
- Fan, X. M., Lian, J. S., Guo, Z. X. & Lu, H. (2005). Appl. Surf. Sci. 239, 176–181.
- Groenen, R., Loeffler, J., Linden, J. L., Schropp, R. E. I. & Van de Sanden, M. C. M. (2005). Thin Solid Films, 492, 298–306.
- Hoon, W. J., Chan, Y. K., Krishnasamy, J., Tou, Y. T. & Knipp, D. (2011). Appl. Surf. Sci. 257, 2508–2515.
- Jong, P. P., Sin, K. K., Park, J. Y., Ok, K. M. & Shim, W. (2009). Bull. Korean Chem. Soc. 30, 114–118.
- Malandrino, G., Balandino, M., Laura, M., Perdicaro, S. & Fragala, I. L. (2005). Inorg. Chem. 44, 9684–9689. [DOI] [PubMed]
- Matthews, J. S., Onakoya, O. O., Ouattara, T. S. & Butcher, R. J. (2006). Dalton Trans. pp. 3806–3811. [DOI] [PubMed]
- 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.
- Sato, H., Minami, T., Miyata, T., Takata, S. & Ishii, M. (1994). Thin Solid Films, 246, 65–70.
- Sheldrick, G. M. (2002). SADABS University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Smith, F. (1983). Appl. Phys. Lett. 43, 1108–1110.
- Tribolate, R., N’tep, J. M., Barbe, M., Lemasson, P., Mora-Sero, I. & Munoz, V. J. (1999). J. Cryst. Growth, 198/199, 968–974.
- Wan, Q., Li, Q., Chen, Y., Wang, T., He, X., Li, J. & Lin, C. (2004). Appl. Phys. Lett. 84, 3654–3656.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104520X/bt5685sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104520X/bt5685Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report