Aqua-[N-phenyl-2-(quinolin-8-yl-oxy)acetamide]dinitratozinc(II).

Abstract

In the title complex, [Zn(NO(3))(2)(C(17)H(14)N(2)O(2))(H(2)O)], the six-coordinated Zn atom is in a distorted octa-hedral geometry, the donor centers being two O atoms and one N atom from the tridentate organic ligand, a water O atom and two O atoms from two monodentate nitrate ions. In the crystal, O-H⋯O hydrogen bonds between the coordinated water mol-ecules and nitrate O atoms and N-H⋯O hydrogen bonds between the main ligand and nitrate O atoms consolidate the three-dimensional network.

Full text

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Aqua[N-phenyl-2-(quinolin-8-yloxy)-
acetamide]dinitratozinc(II)
Wei-Na Wu, Yuan Wang,* Ai-Yun Zhang, Rui-Qi Zhao
and Qiu-Fen Wang
Department of Physics and Chemistry, Henan Polytechnic University, Jiaozuo
454000, People’s Republic of China
Correspondence e-mail: wangyuan08@hpu.edu.cn
Received 13 January 2010; accepted 6 February 2010
Key indicators: single-crystal X-ray study; T = 296 K; mean ?(C–C) = 0.004 A ˚;
R factor = 0.034; wR factor = 0.093; data-to-parameter ratio = 14.3.
In the title complex, [Zn(NO3)2(C17H14N2O2)(H2O)], the six-
coordinated Zn atom is in a distorted octahedral geometry, the
donor centers being two O atoms and one N atom from the
tridentate organic ligand, a water O atom and two O atoms
from two monodentate nitrate ions. In the crystal, O—H???O
hydrogen bonds between the coordinated water molecules
and nitrate O atoms and N—H???O hydrogen bonds between
the main ligand and nitrate O atoms consolidate the three-
dimensional network.
Related literature
For the synthesis of N-phenyl-2-(quinolin-8-yloxy)acetamide,
see: Li et al. (2005); Wu et al. (2006). For the crystal structure
of the hydrate of this molecule, see: Li et al. (2005). For the
coordination ability of related amides to lanthanides, see: Cai
& Tan (2002); Wu et al. (2006).
Experimental
Crystal data
[Zn(NO3)2(C17H14N2O2)(H2O)]
Mr= 485.71
Triclinic, P1
a = 7.9980 (14) A˚
b = 9.5109 (16) A˚
c = 13.359 (2) A˚
? = 94.876 (2)?
? = 96.496 (2)?
? = 106.031 (2)?
V = 963.2 (3) A˚3
Z = 2
Mo K? radiation
? = 1.34 mm?1
T = 296 K
0.30 ? 0.19 ? 0.11 mm
Data collection
Bruker SMART CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
Tmin= 0.745, Tmax= 0.863
10541 measured reflections
4030 independent reflections
3454 reflections with I > 2?(I)
Rint= 0.028
Refinement
R[F2> 2?(F2)] = 0.034
wR(F2) = 0.093
S = 1.05
4030 reflections
281 parameters
H-atom parameters constrained
??max= 0.66 e A˚?3
??min= ?0.39 e A˚?3
Table 1
Selected geometric parameters (A˚,?).
Zn1—O6
Zn1—O3
Zn1—O9
2.0231 (17)
2.0494 (17)
2.0818 (17)
Zn1—O2
Zn1—N1
Zn1—O1
2.1110 (15)
2.1166 (17)
2.2612 (16)
O6—Zn1—O3
O6—Zn1—O9
O3—Zn1—O9
O6—Zn1—O2
O3—Zn1—O2
O9—Zn1—O2
O6—Zn1—N1
O3—Zn1—N1
103.05 (7)
86.57 (8)
170.28 (7)
93.07 (7)
95.75 (7)
85.04 (7)
120.13 (8)
86.60 (7)
O9—Zn1—N1
O2—Zn1—N1
O6—Zn1—O1
O3—Zn1—O1
O9—Zn1—O1
O2—Zn1—O1
N1—Zn1—O1
87.29 (7)
145.38 (7)
163.42 (7)
86.10 (7)
84.93 (7)
72.04 (6)
73.67 (6)
Table 2
Hydrogen-bond geometry (A˚,?).
D—H???A
O9—H9A???O6i
O9—H9B???O4ii
N2—H2???O8iii
Symmetry codes: (i) ?x þ 1;?y þ 2;?z; (ii) x þ 1;y;z; (iii) x;y ? 1;z.
D—HH???AD???AD—H???A
0.82
0.88
0.86
1.99
1.97
2.07
2.803 (3)
2.797 (3)
2.869 (3)
173
155
155
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,
SHELXTL (Sheldrick, 2008); software used to prepare material for
publication: SHELXTL.
2008);moleculargraphics:
The authors are grateful for financial support from the
Henan Administration of Science and Technology (grant No.
092102210363), the Main Teacher Project of Henan Province
(grant No. 649082) and the Doctoral Foundation of Henan
Polytechnic University (B2009–65 648359 and B2009–70
648364).
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: BH2270).
References
Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
Cai, Z.-H. & Tan, M.-Y. (2002). J. Rare Earths, 20, 382–384.
Li, X.-M., Wen, Y.-H., Li, M.-J. & Zhang, S.-S. (2005). Acta Cryst. E61, o2389–
o2390.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wu, W.-N., Yuan, W.-B., Tang, N., Yang, R.-D., Yan, L. & Xu, Z.-H. (2006).
Spectrochim. Acta A, 65, 912–918.
metal-organic compounds
m288
Wu et al.
doi:10.1107/S160053681000471X
Acta Cryst. (2010). E66, m288
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
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Acta Cryst. (2010). E66, m288 [ doi:10.1107/S160053681000471X ]
Aqua[N-phenyl-2-(quinolin-8-yloxy)acetamide]dinitratozinc(II)
W.-N. Wu, Y. Wang, A.-Y. Zhang, R.-Q. Zhao and Q.-F. Wang
Comment
Including our previous work (Wu et al., 2006), the amide type ligands have been widely used to enhance the luminescent
emissions of the lanthanide ions because of their excellent coordination ability (Cai & Tan, 2002). However, little work has
been done on their transition metal complexes. Therefore, as part of our ongoing studies of the amide type ligands, the title
complex was synthesized and characterized by X-ray diffraction.
As shown in Fig. 1, in the title complex, the six-coordinated Zn atom is in a distorted octahedral geometry with the donor
centers of two O atoms and one N atom from the ligand, one O atom from one water molecule and two O atoms from two
nitrate ions. The dihedral angle between phenyl ring and naphthyl ring is 22.5 (1)°.
In the crystal, O—H···O hydrogen bonds between the coordinated water molecules and nitrate O atoms, and N—H···O
hydrogen bonds between the ligands and nitrate O atoms are helpful to consolidate the three-dimensional network (Fig. 2).
Experimental
N-phenyl-2-(quinolin-8-yloxy)acetamide (Wu et al., 2006; Li et al., 2005) (0.278 g, 1 mmol) was dissolved in acetonitrile
(10 ml), then an acetonitrile solution (10 ml) containing zinc nitrate hexahydrate (0.295 g, 1 mmol) was added dropwise
at room temperature. After stirring for 2 h, the mixture was filtered and set aside to crystallize at room temperature for 8
d, giving colorless prismatic crystals.
Refinement
Atoms H9A and H9B (water molecule O9) were located in a difference map and their positions fixed, with Uiso(H) =
1.5Ueq(O9). Other H atoms bonded to C and N atoms were placed in calculated positions and treated using a riding-model
approximation [aromatic groups: C—H = 0.93 Å and Uiso(H) = 1.2Ueq(carrier C); methylene group: C—H = 0.97 Å and
Uiso(H) = 1.2Ueq(carrier C); amine group: N—H = 0.86 Å and Uiso(H2) = 1.2Ueq(N2)].
Figures
Fig. 1. The molecular structure shown with 50% probability displacement ellipsoids.

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Fig. 2. The crystal packing for the title complex via hydrogen bonds (dashed lines).
Aqua[N-phenyl-2-(quinolin-8-yloxy)acetamide]dinitratozinc(II)
Crystal data
[Zn(NO3)2(C17H14N2O2)(H2O)]
Mr = 485.71
Z = 2
F(000) = 496
Dx = 1.675 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4639 reflections
θ = 2.6–26.4°
µ = 1.34 mm−1
T = 296 K
Prism, colorless
0.30 × 0.19 × 0.11 mm
Triclinic, P1
Hall symbol: -P 1
a = 7.9980 (14) Å
b = 9.5109 (16) Å
c = 13.359 (2) Å
α = 94.876 (2)°
β = 96.496 (2)°
γ = 106.031 (2)°
V = 963.2 (3) Å3
Data collection
Bruker SMART CCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
Tmin = 0.745, Tmax = 0.863
10541 measured reflections
4030 independent reflections
3454 reflections with I > 2σ(I)
Rint = 0.028
θmax = 26.7°, θmin = 2.2°
h = −10→10
k = −11→11
l = −16→16
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.034
wR(F2) = 0.093
H-atom parameters constrained
S = 1.05
w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1851P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.66 e Å−3
4030 reflections
281 parameters

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0 restraints
Δρmin = −0.39 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
0.40610 (3)
0.3965 (2)
0.2694 (2)
0.1934 (2)
−0.0719 (3)
0.0289 (3)
0.4097 (3)
0.3915 (4)
0.3628 (4)
0.6309 (2)
0.6102
0.7372
0.5583 (2)
0.2226 (3)
0.2306
0.0477 (3)
0.3863 (3)
0.6333 (3)
0.6103
0.7469 (4)
0.7961
0.7839 (4)
0.8605
0.7068 (3)
0.7382 (4)
0.8126
0.6612 (4)
0.6842
0.5464 (4)
0.4958
0.5119 (3)
0.5925 (3)
0.3655 (3)
0.2877
0.4750
0.2808 (3)
0.1501 (3)
0.1263 (4)
0.1577
0.0558 (4)
0.0408
0.0081 (4)
−0.0394
y
0.96202 (3)
0.74601 (17)
0.78947 (17)
0.9611 (2)
0.9596 (3)
0.9897 (3)
1.1192 (2)
1.2818 (2)
1.3175 (2)
0.9394 (2)
0.9205
0.9403
1.0166 (2)
0.5535 (2)
0.4695
0.9699 (2)
1.2425 (2)
1.1531 (3)
1.2301
1.1865 (3)
1.2840
1.0767 (3)
1.0985
0.9290 (3)
0.8075 (4)
0.8223
0.6687 (4)
0.5897
0.6413 (3)
0.5456
0.7573 (3)
0.9046 (3)
0.6234 (3)
0.5363
0.6033
0.6650 (2)
0.5535 (3)
0.4259 (3)
0.3465
0.4166 (3)
0.3311
0.5329 (3)
0.5267
z
0.180722 (18)
0.24213 (12)
0.06551 (12)
0.25329 (13)
0.26368 (17)
0.12235 (16)
0.08737 (14)
0.20478 (17)
0.04674 (17)
0.12457 (14)
0.0626
0.1513
0.32636 (13)
−0.00405 (15)
0.0117
0.21100 (16)
0.11447 (17)
0.36958 (19)
0.3375
0.4625 (2)
0.4912
0.50957 (19)
0.5703
0.46704 (17)
0.5099 (2)
0.5711
0.4632 (2)
0.4927
0.37011 (19)
0.3383
0.32834 (17)
0.37403 (16)
0.16737 (18)
0.1880
0.1567
0.07116 (17)
−0.10558 (18)
−0.1706 (2)
−0.1465
−0.2714 (2)
−0.3150
−0.3068 (2)
−0.3744
Uiso*/Ueq
0.03178 (10)
0.0397 (4)
0.0379 (4)
0.0468 (4)
0.0721 (6)
0.0820 (8)
0.0524 (5)
0.0757 (7)
0.0769 (7)
0.0566 (5)
0.085*
0.085*
0.0337 (4)
0.0401 (5)
0.048*
0.0447 (5)
0.0480 (5)
0.0450 (6)
0.054*
0.0530 (7)
0.064*
0.0528 (7)
0.063*
0.0431 (6)
0.0566 (7)
0.068*
0.0608 (8)
0.073*
0.0510 (7)
0.061*
0.0370 (5)
0.0343 (5)
0.0411 (5)
0.049*
0.049*
0.0339 (5)
0.0381 (5)
0.0494 (6)
0.059*
0.0610 (8)
0.073*
0.0629 (8)
0.076*
Zn1
O1
O2
O3
O4
O5
O6
O7
O8
O9
H9A
H9B
N1
N2
H2
N3
N4
C1
H1
C2
H2A
C3
H3
C4
C5
H5
C6
H6
C7
H7
C8
C9
C10
H10A
H10B
C11
C12
C13
H13
C14
H14
C15
H15